Matchmaker 101
by Ava Brett
Summary: For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything for him and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined he's going to get it! (A/U coffee shop fic) (Destiel, Sam/Jess)
1. It's way too early to be out of bed!

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below piece of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**Welcome to Matchmaker 101!**

**This is part one of a two parter story which is mainly done by Sam's and Jessica's point of view. The second part to the story will be done by both Dean's and Castiel, however this has not yet been written as I'd like to finish this story first before I start on the next one.**

**I try and update as often as I can but it's not always easy to do due to real life getting in the way, however please be patient with me. Matchmaker 101 and the second story will be completed; I have no intention of abandoning either of them.**

**Anyway please enjoy chapter one**

**Thanks**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**Sometimes the early bird does catch the worm… Sam just wishes it wasn't quite so early!**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**Hints of Castiel Novak/ Dean Winchester though nothing concrete yet.**

* * *

Chapter One

It's way too early to be out of bed!

* * *

"Come on Dean do we actually have to be here today? It's way too early to be out of bed" Sam complained staring at the back of his older brother's head as Dean inserted the key into the lock of the coffee house door and turned it. He turned to look at Sam, a look of amusement on his face which caused Sam to glare at him. It seriously wasn't fair. Dean looked like a stupid ass model that had simply rolled out of bed looking wide awake and perfect while the glance Sam had in the mirror that morning revealed that he looked like an extra for one of the un-dead movies. His skin had been pale, his hazel eyes bloodshot with bags underneath big enough that he could probably have stored shopping in them while his light brown hair had stood up on end looking like he had stuck it in a plug socket during the night and electrocute him self.

He needed a haircut, he needed a shave and he seriously needed to be back in bed sleeping rather then standing in the freezing cold, hands jammed under his armpits while he waited for Dean to hurry the hell up so he could get inside into the warm.

"It's six on a Saturday morning Sammy, it's not like I've dragged you out of bed at three on a Monday morning, I could understand you bitching if I had done that." Dean replied sounding as amused as he looked. Sam rolled his eyes, reaching out and pushing Dean through the door. He quickly shut the door behind him, breathing a sigh of relief as warmth moved over him as he stamped his feet against the mat.

An unwilling smile came to his mouth as he looked around the large room, blinking in the sudden bright light as Dean flicked on the switch by the doorway. Sam had to hand it to his brother; he certainly had built up a place he could be proud of. The room was spacious and clear of clutter while still managing somehow to produce a cosy feel to the room. Squishy dark brown chairs surrounded tables which were spaced with enough room that people could get round them without any problem and could have conversations without worrying about being overheard by anyone. The walls were a light cream colour covered in black and white photos of the surrounding area while the floor was dark brown floorboards.

Sam would never admit it to Dean but the Impala coffee shop had to be one of his favourite places to go.

"You know six in the morning is still freaking early Dean, way too early for anyone to actually be up and thinking about coffee" Sam replied aware that his voice was barely escaping a whine; Dean looked back at him with a raised eyebrow. "You know who is up at six on a Saturday morning Dean?" he demanded, continuing without waiting for an answer "Crazy people, that's who."

"Or maybe just people who have jobs that require them to be up early on a Saturday morning Sam, I can guarantee that they are thinking about coffee right about now, in fact it's probably one of the only things they are thinking about right about now." Dean pointed out as he reached up and dragged the dark grey beanie hat he was wearing off of his head, throwing it onto one of the tables, his gaze moving away from Sam to focus on the large ticking clock behind the counter.

"Yeah crazy people" Sam replied under his breath. Dean turned back to Sam speaking as he began undoing the buttons on his thick winter coat. He looked like the Michelin man, completely bundled up against the cold outside, though somehow the look suited him making Sam hate him for a moment. Dean could wear a bin bag and still look fantastic, it seriously wasn't fair.

"Look Sam, I'm not being funny but you're the one who begged me for some shifts because you needed the extra cash remember. I had to endure a boring ass lecture from you which lasted over a hour about how if I need anything from you then all I had to get off my high horse and ask you blah, blah, blah. I ask you once, just the once to help me open up on a Saturday morning because Anna is sunning it up somewhere on holiday and all you've done from the moment I picked you up this morning is moan and bitch at me about everything. If it bothers you that much then freaking go home, I'll cope alone, it's not like I haven't opened this place up by myself before. Hell I've lost count on the number of times I've done it alone; it's seriously not a big deal."

Sam bit the inside of his cheek, shrugging his shoulders as he pulled his gloves off throwing them on top of Dean's hat on the table surface.

"Okay so maybe just maybe I've been bitching slightly" he admitted, a reluctant smile coming to his face when he caught the disbelieving expression on Dean's face. "Okay you've got me I'm bitching like a spoiled little brat. I'm just tired Dean that's all and I look like a tramp" he whined reaching up and running a hand over his stubble "But cut me a break okay, I was up until three o clock this morning studying for a big ass exam which is next week and when I say big I really mean that it's a really big deal."

Dean frowned back at him as he walked to the counter slipping behind it.

"When you say a big deal Sammy how big a deal do you mean exactly?" his brother asked curiously bending down behind the counter probably checking the state of things. Sam frowned at the question before he shrugged off his jacket, unwinding his scarf from around his neck.

"Well, a third of my grade sort of big deal Dean"

Dean's head suddenly appeared, an exasperated look on his face as he rested his hand on the counter still hunched down, the other hand reaching towards his face so he could pinch the bridge of his nose, his green eyes turning towards the ceiling as though he was asking God for some form of strength so he could deal with Sam without strangling him.

"Then why the hell are you here Sam?" Dean demanded, speaking slowly and clearly. "You should have said something about it sooner to me" Sam watched as Dean stood, pointing a finger to the closed door "Go home and get some sleep because I've gotta be honest with you bro, you look like shit. Get some studying done once you've rested up a bit. I'll be fine here until Jo gets in for her shift later on."

"Yeah but when is Jo due in exactly?" Sam asked suspiciously, his eyes narrowing slightly as he waited for an answer. Dean shrugged.

"Her shift starts at Midday" he answered.

"No way then Dean" Sam replied back bluntly "I was the one who said yes when you asked me to help, it wasn't like I didn't know about the exam. I'm not going to leave you in the lurch dealing with this place by yourself on a Saturday when I know it's gonna be rammed, while I go back and sleep. What kind of a jerk do you think I am that I'd do that to you of all people?" he demanded sounding outraged. "Now get the damn coffee machine on so I can have a cup before the doors open in twenty five minutes admitting the crazy people and this coffee better be on the house Dean or I'll be forced to kick your ass my self."

"I'd like to see you try" Dean said with a laugh as he shook his head "Beside Sammy boy when exactly have I ever charged you for anything in here?" Dean remarked switching on the coffee machines which produced a strangely comforting hum in the air. "Though you know with the sheer amount of my cake you eat I'm beginning to think I should to save you from yourself before you get too fat to move your ass" Sam patted his trim stomach.

"You wouldn't dare" Sam taunted back. "Beside you never have done before. Not once and you don't allow the others to charge me either. In fact the last-"

"Sam I swear to god if you don't stop with this chick flick moment I'm gonna have to kill you and dispose of the body. It's way too early in the morning for this shit. If you want to stay then I'm not gonna say no but if you want to go then I'm not gonna kill you for leaving, you'd just owe me a favour which I can cash in any time I want to in the future and I mean any favour" Dean warned with a smile.

"You're such a jerk!" Sam commented feeling a rare wave of affection towards the older man; He rubbed his hands together glancing around him before he looked back at his distracted brother. "This is normally the bit where you tell me what you need me to do Dean, unless you want me just to stand here and look pretty for the customers when they arrive."

"Yeah you're more likely to scare them off looking like you do at the moment Sam" Dean retorted as he rolled his eyes at him before he began giving him instructions on what he needed to do.

They worked in a comfortable silence, moving around each other and getting things ready for the morning rush, the CD player on filling the coffee shop with the strains of the electric guitar and the beats of the drums. Dean had always listened to classic rock for as long as Sam could remember.

There had been countless mornings which had began in this same way though often Sam had been sitting at one of the tables trying to get some extra studying done before his morning classes. Dean had brought the shop out of the blue when Sam had accepted his offer to attend Stanford University. The boys had moved from Kansas to California with nothing but what they could fit in their car, renting out their old apartment. Why Dean had decided on a coffee shop was beyond Sam but he was certainly glad. The place had been a roaring success from the moment it had opened, attracting the members of the student body into it as well as the countless of other offices and shops which all needed the same shot of caffeine in their veins to start the day.

Sam didn't know how Dean did it, working all day in the coffee shop before heading over to the Roadhouse bar three times a week and working until the early hours of the morning. Hell his brother even did a shift on Sunday at the Bobby Singer's garage. The few times he had asked Dean about why he did it his brother would simply shrug reminding Sam that his scholarship didn't cover everything and therefore they needed the money to survive. Sam wasn't working and therefore as far as Dean was concerned it was his duty as his older brother to support him until he was.

He wondered whether Dean even had a life, did he have friends? Did he go out? Hell did Dean even date anyone because Sam couldn't work out where the time would come from if he did. If Dean wasn't working then he tended to be sleeping trying desperately to keep up with all the demands on his time.

The thought that Dean might be sacrificing his life for Sam made him feel sick to the pit of his stomach.

"Hey!" Sam jumped as Dean's hand clapped down on his shoulder. "Did you hear what I just said to you Sam?" his brother asked, a flicker of concern coming to his eyes. Sam shook his head ignoring the annoyed look which came to Dean's face.

"No what's up?"

Dean jerked his head to the clock.

"It's time to open up sunshine" Dean said slowly. Sam nodded his head, walking to the door and flipping the sign to open; he peered through the glass and shivered at the sight. Snow lay thick on the ground, the sky heavy and dark clearly threatening snow again before the day was through. He should have thought ahead and brought his own car with him that morning but it would have taken too much time to make it ready for the road and the conditions. It had been easier to accept Dean's offer to pick him up on his way.

"Here maybe this will help wake you up a bit" Dean remarked, Sam glanced around as a large mug of coffee was thrust into his hand, he lifted it and smelt it, a grin coming to his face as he recognised the sweet smell of vanilla. His brother knew him too well.

Sam stepped behind the counter just as the door was pushed opened revealing the first cold looking customer of the day. Sam concentrated on taking the orders and getting any cakes of pastries ready, while he watched Dean work from the corner of his eye as the older man swiftly produced the drinks, lightly flirting and chatting with all the customers who clearly adored him if their smiles and familiar banter were anything to go by.

"One tall black Americano with an extra espresso shot please" a gruff voice stated. Sam glanced back to the front of the counter to see a tallish man standing there. He was pale with wild dark hair and bright blue eyes. He looked briefly at Sam before his gaze flickered towards Dean and stopped there as though he was unable to look away. Sam raised an eyebrow as he saw a pink flush cover the man's cheekbones as his mouth fell slightly open. Sam glanced towards Dean unsurprised to see that his brother hadn't even noticed the man or the attention he was receiving from him. For someone who was such a natural flirt Dean was half dense when it came to realising that people were coming onto him.

"Name" Sam asked briskly. The man looked away from Dean with obvious difficulty, a look of embarrassment coming to his face at being caught so obviously staring, his gaze lowered to the counter top.

"Castiel" he answered, Sam nodded.

"Takeaway or are you drinking in today?"

"It's for takeaway thanks"

"Right that will be two dollars fifty then please" Sam stated, ringing it up on the till and taking the five dollar bill from the man, he quickly counted the change out and handed it over to him, pointing down to the end of the counter where two blond students were giggling with each other staring at both Sam and Dean as though they wanted to order them off the menu. Sam grinned; the job certainly had perks at time. "Head over there to collect your order" he remarked. Castiel nodded and headed away from the counter to where Sam had indicated looking around him awkwardly, his eyes lingering on the photos on the wall with a look of interest.

He must have been a new customer because Sam couldn't remember having seen him before. There was no one waiting to be served so Sam turned his attention to Dean ready to chat with his brother once Castiel's drink order was finished, it was the first time since they opened that they had had any sort of break from serving.

"One tall black Americano with an extra shot of espresso for-"Dean turned the cup round "Castiel?" Sam caught his eyes quickly, hiding a grin as he nodded his head towards the man patiently waiting for his drink at the end of the counter.

Dean turned from him, meeting Castiel's eyes for the first time. Sam watched in surprised when Dean's mouth fell open into an O of surprise before he looked quickly away, his hand still held out to Castiel, offering the other man his drink.

Castiel took the coffee, his fingers brushing Dean's as he thanked him. Sam eyebrow rose when Dean blushed at the contact, Dean who never blushed over anything.

"Yeah no problem" Dean muttered. Sam watched as Castiel's serious expression melted into a slight smile, his eyes searching Dean's face before he spoke again.

"Goodbye."

"Err yeah see ya" Dean answered, his gaze fixed on the older man as he turned and walked away, disappearing out of the door into the darkness outside. For a moment Dean stared after him looking stunned before he shook his head and began to busy himself with cleaning the coffee machine.

Sam grinned.

Now that had been highly interesting.

* * *

Author Note

**Thanks for taking the time to read!**


	2. Operation Big Brother is a go

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters which are mentioned in the below work of fan fiction belong to me in any shape or form. I am merely using them for my own entertainment purpose**

Author Note

**Here's chapter two for you all to consume!**

**I do like writing sneaky Sam and Jess so no doubt we'll be seeing it a lot more in the rest of the story as well.**

**Hope you all enjoy it!**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**I'm in, if you're in…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**Mentions of Castiel Novak/Dean Winchester**

* * *

Chapter Two

Operation Big Brother is a go

* * *

The next time Sam saw his brother interact with Castiel was two days later.

He had been in the middle of studying in the large campus library for his next exam when he had suddenly been struck by a craving for one of his brother's freshly made cakes, he had tried to ignore it but it had been impossible, the more he had tried the more he found himself desiring one. Giving it up as a bad job he had swiftly packed his belongings up, wrapping his scarf around his neck before he shrugged his heavy winter coat on and left the warm library for the bitter cold world outside.

He really hoped that Dean had made the lemon cake which simply melted away in your mouth; Sam could happily eat a whole cake to himself if he was ever given the opportunity to. He had managed it once when Dean had been distracted by something and it had been so worth it in Sam's eyes, not only because it had been gorgeous but also because of the half proud, half disgusted look which had come to Dean's face when he realised what Sam exactly had done when his back had been turned.

Now he thought about it he hadn't actually seen or spoken to his brother since the last time he had worked a shift with him and he felt a small flare of guilt at the fact. He would have to make it up to Dean once his exams were finally done and dusted.

It took exactly seven minutes to reach Dean's coffee shop from the library and Sam had never been so grateful to see it before in his life. He held the door open for a group of stressed looking teenagers before he entered, taking a deep breath and smiling as the familiar smell of coffee and baked goods hit his senses making his mouth water.

He pushed the door closed behind him and looked around him, raising an eyebrow when he saw just how crowded the room was for a Monday afternoon, most of the clientele looked like they were students if the textbooks and laptops open on the table surfaces were any indication to go by, clearly some of the afternoon classes had been cancelled and they were making the most of a free period to ply themselves with caffeine to get them through their next lecture.

Sam could see his brother working hard behind the counter, preparing the drinks and keeping an eye on something to the side of him. Knowing Dean he had spent his lunch break whipping up some new cakes to keep them from running out which had happened on more then one occasion if Sam's memory served him correctly. It certainly would explain the gorgeous smell which was making his stomach rumble violently, reminding him with a vengeance that he hadn't actually eaten anything since seven o clock that morning when he had grabbed a piece of slightly burnt toast before racing out of his dorm room to make his morning lecture in time.

Sam stomped his feet against the mat trying to dislodge the snow from them before he lifted his arm and waved it in Dean's direction. The older man glanced up, clearly catching the moment and smiled at him, his eyes warming as they met Sam's gaze. Sam grinned back before pointing to one of the tables by the window which had just become vacant. Dean nodded, holding his finger up to indicate he would be with him in a moment before he turned his attention back to the drink he was making.

Sam waved at Chuck Shurley, his grin widening when the other man shot him a suspicious glance before he carried on taking orders from the long queue which had formed in front of him. Sam didn't mind Chuck though he could never resist teasing the older man when given the opportunity. He was just so easy to wind up. Sam had no idea how Dean put up with him on a daily basis though, if it had been Sam then he probably would have strangled Chuck within a week of working with him, however the two men did appear to get on much to Sam's disbelief.

He came to a stop by the table and dropped his bag onto one of the chairs surrounding it to save it from being grabbed by anyone else before he took his coat and scarf off throwing them on the back of the same chair before he sat down, rubbing his hands together to try and warm them up, leaving his gloves at home that morning in his rush to reach the campus on time for his lecture had been a seriously stupid mistake for him to make.

Sam pulled a face as he stared out of the window at the dark grey sky wishing for the hundredth time that the snow would just disappear already. Sam loved the snow normally, he really did but he didn't love it when he had to go out into it constantly. It was hard to concentrate when you were freezing cold and the bottom of your jeans was wet and clinging uncomfortably to your lower legs. No the sooner the weather changed and became dry and sunny again the better it would be in his eyes.

Shaking his head Sam pulled his bag over to him, unzipping it and taking out his mobile phone, his laptop and the textbook he needed for his next law class. He glanced at his phone smiling when he noticed that he had a received a text message from Jessica Moore, a friend he was due to be meeting. He read it and quickly responded to it. Once that was dealt with he powered up his laptop, leaning back in his chair as he waited impatiently for either Jessica to arrive or for Dean to have a spare second to come and say hey to him.

Sam found his eyes flickering back to the counter and focused on his brother with a narrowed look as he felt concern trickle through him. God his brother looked exhausted. If he had been working late last night then he wouldn't have gotten into his apartment until at least two in the morning, perhaps even later if closing up had taken more time then it normally did. If Dean had opened the coffee shop up that morning as well then that would have had him out of his home by five thirty, both of which pointed to the fact that Dean was going to burn out if he continued the way he was going. Sam was going to have to attempt to have yet another word with him and hope against hope that it would actually sink in this time around rather then Dean brushing off his concern as an overreaction.

Shaking his head, Sam turned away from his brother and focused his attention on his laptop, bringing up the last word document he had been working on and reading through it to make sure that it made sense and that he hadn't made any stupid mistakes in his rush to get it done.

"Hey Sammy boy"

Sam blinked at the interruption, looking up in surprised to see Dean standing next to his table, a white plate held in one hand while his other was curled round the handle of a large white mug.

"Dean?" he said, glancing at the time quickly, his eyes widening when he realised he had been studying for at least thirty minutes.

"Sorry its taken so long to get to you but the queue just wouldn't die down" Dean commented, jerking his head back towards the counter, Sam followed his gaze, a grin coming to his face when he noticed Chuck slumped against the counter, resting his face in his hand looking exhausted as though he had been running a marathon. "You gonna shove the book over so I can put these down or do you just want me to stand here holding your stuff? If you don't want them I'll give them to Chuck or something, he looks like he could use an instant pick me up" Dean asked with a raised eyebrow.

"Don't you dare" Sam responded, pushing his textbook back into his bag freeing up the space and allowing Dean to put both the plate and mug down.

Sam looked at them both, his mouth watering as he realised with mounting glee that Dean had brought him over a slice of lemon cake and not only that but it was a damn big slice as well. Sam could have jumped up and hugged his brother right then and there, only the knowledge that Dean was likely to punch him if he did kept him from doing it.

Sam didn't hesitate, grabbing his fork and plunging it into the lemon cake, tearing off a piece which he swiftly stuffed in his mouth, his eyes closing as he gave a moan of pleasure. Jesus Christ he would commit murder in the name of this cake.

"Try and remember that this is a family place Sam, don't make me have to throw you out for making explicit noises while eating a slice of cake" Dean teased him.

"Yeah well don't make it so damn good and we wouldn't have this problem would we" Sam responded, looking past his brother as the door opened admitting a fresh wave of frozen looking people, he looked back to Dean who had followed his gaze with a sigh. "You know I didn't think it would be so packed in here today considering what the time is" Sam remarked, putting his fork down for a moment so he could grab his mug and take a sip of the vanilla latte which Dean had perfected down to a fine art.

"Its often like this Sammy boy, you're just normally not here to see it." Dean said, glancing back at the counter. "You just come here to study today?" he asked curiously, eyes dropping to the text book as he took a step away from Sam in the direction of the counter.

"Yeah, I'm meeting Jess here any minute now" Sam answered, running a hand through his hair. "She texted me a short time ago saying she was running late so I figured that I might as well start without her" Dean nodded, a smile curling his mouth as he wriggled his dark eyebrows up and down.

"Jess huh" Dean commented tapping his finger against his lower lip thoughtfully, "Are we talking about the very same Jess who you won't shut about or is this a different one?"

Sam rolled his eyes, hating the fact that he could feel the familiar feeling of heat across his cheekbones meaning he was blushing yet again.

"Ooooooooo Sammy you're going red" Dean stated gleefully, laughing when Sam flipped him the finger.

"Don't you have some customers to serve or something?" Sam asked haughtily causing Dean to roll his eyes as he held his hands up in surrender.

"Fine! I know when I'm not wanted. Get my attention if you need anything else though it better not be cake! I'm not gonna be responsible for you getting fat Sammy" He grinned a final time before he turned and walked away, skirting around the crowded tables and smiling at the patrons who tried to catch his attention until he was back behind the counter.

Sam shook his head, taking another sip of his drink as he began reading again, highlighting the odd sentence and deleting it when he realised it made no sense.

"Hi Sam, sorry I'm late, you haven't been waiting ages for me have you?" Sam glanced up in time to see Jessica Moore pull out the seat opposite him. "I can't get over how flipping cold it is outside, I thought California was meant to be warm, I mean it's called the sunshine state for god sake" she stated, unbuttoning her coat and slipping it off. "Do you want anything? I could kill for one of the Hazelnut hot chocolates they do here, I don't know what the guy who makes them does but they are like heaven in a cup. Jesus its busy here, is it always like this?"

"You might want to try and breath Jess before you collapse from lack of oxygen" Sam pointed out in amusement when Jessica finally stopped to catch her breath.

"Well aren't you a riot today, I'm fine as you well know Sam" she assured him with a laugh, her gaze turning to the long queue, she pulled a face, grabbing her purse out of her handbag before she turned back to him with a questioning look. "Did you want anything Sam?"

"I've got this, Hazelnut hot chocolate right?" Sam stated, pushing himself to his feet and raising his hand into the air. He waited until Chuck looked up at him before he pointed towards Dean. Chuck rolled his eyes at him before he leaned across and poked Dean in the ribs, Sam caught the pissed off expression on Dean's face and wondered vaguely what his brother said to Chuck to have him suddenly look so flustered. He waved his hand at Dean plastering an innocent look on his face when he saw the annoyed look fade from Dean's face into a questioning one. Sam pointed at Jessica who was watching the scene with a raised eyebrow and mouthed her drink order to him, giving his brother a thumb up when Dean nodded, holding up one finger to indicate that he would have it in a minute.

"Err so what was all that about exactly?" Jessica asked as they both took their seats. She eyed his lemon cake hungrily but he pretended to ignore it, no one shared his cake with him, not even Jessica. "Do you know the guy behind the counter or something?"

"Just a bit" Sam responded, closing the top down on his laptop and focusing his full attention on Jessica. "The one making the drinks is my older brother Dean; he's actually the owner of the place. It's kinda a perk of being family that you get to bypass the queues. The other is the fact that I get to be his guinea pig when it comes to trying his cakes." Jessica's eyes widened as she looked around her carefully.

"You're lucky he's so nice to you then" she stated, leaning forward and resting her elbows against the table surface. "If my older brother Mark owned this place then I can guarantee that he would make me queue just like everyone else." Sam shrugged.

"I guess I am lucky" he responded "It's just Dean for you, he can be pretty awesome sometimes other times though he can be a complete asshole but that's life I guess."

"Seriously though Sam, I really like what he's done with the place here, its no wonder it's packed every time I pass it or come in for a drink."

"Yeah I know its crazy right, just do me a favour and be sure to let him know that you like it when he comes over with your drink, he never believes me when I tell him how great the place is, he just brushes the comments off but maybe if you say it then he'll listen for once." Sam sighed, leaning back in his chair; he tilted his head to the side casually before his eyes suddenly widened as he took in the familiar looking man dressed in the tanned trench coat from the other day, the one who Dean had actually reacted to when he had seen him.

Sam had tried to question Dean about what had happened once the man had left but his brother had gone surprisingly closed lipped over the whole incident, finally snapping at Sam to get on with his work rather then gossiping like a woman.

Dean hadn't noticed the man yet but the dark haired man had most definitely clocked Dean if his intense unwavering stare was anything to go by. Sam bit down on his lower lip, staring at him with a narrowed gaze as he tried to remember what the man's name was. Cassius, Cassiel. He suddenly clicked his fingers. Castiel that had been the guy's name. He was surprisingly still, Sam had often taken to observing people when he had been bored and he had noticed that people always tended to fidget whether they realised they were doing it or not, just small things such as moving from foot to foot, or playing with their hands or with an item of clothing but not Castiel, he remained as still as a statue and merely stared at Sam's brother in a way that made Sam almost feel sorry for Dean.

He watched as his brother finally looked up from the drink he was making, his face flushing as his eyes widened at the sight of Castiel. Sam's eyebrow shot up when he saw Dean fumble with the cup he was holding, a look of pain crossing his face when the hot liquid spilled over his hand. Sam made a move to get up before he stopped himself knowing that it would have been the last thing Dean wanted, his brother turned, shoving the injured hand under the cold water tap saying something to Chuck, no doubt reassuring him that he was fine. Sam looked back to Castiel surprised to see the concerned look on the older man's face. He was fidgeting on the spot now, his fingers flexing as though he wanted to vault over the counter and check on Dean himself to make sure he was okay.

"Is the guy in the trench coat your brother's boyfriend or something?" Jessica suddenly asked attracting Sam's attention back to her, he blinked at her question.

"What makes you say that?" he asked dumbly. Jessica shrugged.

"Because he hasn't taken his eyes off of your brother since he stepped through the door and he looks ready to self combust on the spot because Dean has hurt himself. Of course I might be completely wrong, maybe the guy just really, really like the drinks here" Jessica ended with a smirk.

"I don't know how he feels but from what I've seen I think Dean likes him." Sam commented absently, watching as Dean brushed Chuck's concern away and began serving the drinks again.

"So if they haven't hooked up yet then maybe they will" she remarked casually, looking between the two men thoughtfully. Sam shrugged.

"I doubt it, you don't know Dean Jess. It's like he's allergic to being happy or something. The minute something comes up which makes him happy he gets rid of it or finishes the relationship" Jessica sat back in her chair clearly waiting for him to continue. "I think it's to do with me if you want the truth. I don't think Dean will allow himself to be happy until I am, he's given up a lot for me you know and I doubt it will ever change."

"Well then Sam" Jessica said after a pause "Perhaps its time that you took matters into your own hands instead. If Dean won't do this for himself because of you then perhaps you should do it for him instead" Sam turned to the counter watching when Castiel managed to catch Dean's gaze with his own, it was as though the world suddenly stopped spinning for the pair of them, as if everyone and everything simply ceased to exist. It would have almost been sweet if it didn't threatened to make Sam gag on the cuteness of it all.

"Yeah great idea and all Jess but I wouldn't know how to go about even starting it" he responded, picking up his fork and taking another large bite of cake, he looked up surprised to see Jessica watching him with a amused, calculating expression on her face.

"Well it's probably a good thing that you know me then Sam Winchester because I happen to be an expert at getting people together. I can show you the way to go about it if you want, your brother will be off the market and happy by the time we're finished with him. Just give the word and we'll start"

Sam glanced once more at Dean's face and the way it had lit up before he looked back at Jessica, an answering smirk coming to his face as he nodded his agreement.

"Where do we begin?"

* * *

Author Note

**Thanks for taking the time to read **


	3. Listen up Sam, this is stage one

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below piece of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**Next chapter is complete and ready to be read **

**I am liking writing the banter between Sam and Jess, it's kinda fun **

**Anyway enjoy**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything for him and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined he's going to get it!**

Chapter Summary

**Jessica fills Sam in on stage one of the plan…**

Overall Romances

**Castiel Novak/Dean Winchester and Jessica Moore/Sam Winchester**

Chapter Romance

**Mentions of Castiel Novak / Dean Winchester**

* * *

Chapter Three

Listen up Sam, this is stage one…

* * *

"So where exactly are we meant to start then?" Sam asked as he dumped his bag to the ground and slipped into the spare seat opposite Jessica ignoring the glares he received from the other studying students surrounding them. Jessica had texted Sam while he had been in his previous lecture telling him to get his ass to the library so they could discuss stage one of operation big brother.

Sam had raised his eyebrow in disbelief when she had first used the term to describe their plan but Jessica had been adamant about it so Sam had given in and agreed that it could be called that.

Jessica looked up at him with a raised eyebrow as she reached up and slipped her glasses off of her nose, putting them on her open textbook.

"Well normally you would start by saying hello Sam" she remarked casually. Sam winced, feeling his face flush at the lightly spoken reprimand.

"Hello Jess" he said with a sheepish look. "Sorry I'm late but the lecture ran over by ten minutes" Jessica smiled at him, shaking her head before she leaned forward, resting her forearms on the table surface, her eyes fixed on him in a thoughtful expression which automatically placed him on guard. He might not have known Jessica for long but he certainly had known her long enough to recognise that look as trouble.

"We've got a few things we need to straighten out for this plan to work Sam" she remarked seriously, reaching up and tucking a stray curl which had escaped her ponytail behind her ear. "Firstly, do you want to keep what we're doing a secret from your brother or would you rather we told him what we were going to do?"

"There's not way we're telling Dean" Sam responded instantly "If he ever got wind of it then he would hand me my ass for interfering. No, this is a secret between the pair of us"

"Why would he hand you your ass if you were helping him?" Jessica asked curiously, leaning back and crossing her arms across her chest. Sam shrugged.

"Because he's Dean" Sam stated simply, catching her unimpressed look he continued to explain. "Look Jess the thing you've got to realise about my brother is the fact that he hates anyone trying to interfere in his life or his business. He always has and he always will, our Dad was quite controlling when he was around and it affected us both differently"

"Right" Jessica said slowly, dropping her gaze to the table. Sam spoke.

"Beside Dean is completely allergic to what he calls Chick flick moments, the second anyone in his life makes the mistake of showing they care he freaks out and pushes them away, even with me. It's like he's afraid of being hurt so badly that he can't function when it comes to it so he simply gets rid of whatever is making him uncomfortable in the first place."

"Well that makes things slightly harder" Jessica said before shrugging her shoulders and meeting Sam's directly. "But not impossible, we just need to change the game slightly. So you're brother is out and I'm guessing you've never even said hello to the other guy before let along had a conversation with him right?" she asked.

"I asked him if he was having takeaway or drinking in" he teased. Jessica laughed, rolling her eyes.

"Yeah maybe not quite the connection we needed for this to work" she pointed out, biting down on her lower lip thoughtfully. Sam watched the movement, looking away when he realised what he was doing.

"What about the other people who work at the coffee shop? Do you think any of them would be willing to help us?"

"Probably all of them" Sam admitted as he went through a mental list of the people Dean hired. "The only one who might not would be Anna but that's because she likes him herself. I think she's on holiday for a week or something so she shouldn't be around to interfere in what we're doing" Sam remarked, tapping his fingers lightly against the cover of Jessica's book.

"Well Dean is hardly hard on the eyes to look at, so it's not that big a surprise that people have crushes on him" Jessica remarked offhandedly "And you're positive that you haven't seen him react this way to anyone else before right?"

"Right" Sam replied watching as Jess considered his words carefully before she looked up at him.

"Okay, first things first then is finding out as much as we can about the guy your brother likes, Castiel didn't you say his name was?" she suddenly asked, an amused look coming across her face when he nodded. "Well in that case we need to find out how often Castiel goes into the coffee shop? Does he interact with anyone while he's in there? Is he always alone when he comes in or do other people sometime go in with him? If he has the same routine then you could ask the people who are down to work those shifts to talk to him, see whether they can drag any information out of him that we can use, like if he likes something that Dean likes for example. The more information we have on Castiel the easier it will be to use it in our favour."

Sam nodded with a slight thoughtful frown.

"I can speak to the others and get that arranged." he confirmed.

"Hey" Jessica suddenly said, attracting his gaze and smiling at him. "Just trust me Sam; I know exactly what I'm doing here. You do want Dean to be happy right?" she asked.

"Stupid question Jess" Sam said shortly, shaking his head at her.

"Exactly, even a blind person can see that the pair of you are close to each other. The last thing you want to do is have a hand in setting your brother with a complete and utter loser who is only gonna make him unhappy. This might take slightly longer but it will be worth it in the end, trust me"

"Ok, so we find out whether Castiel is good enough for Dean" he agreed. "And then what do we do? Throw the pair of them into the store cupboard and lock the door behind them hoping they'll make out or something?" Sam asked, stopping suddenly and pulling a face. "Jesus now that was a thought I could have lived without having in my brain" he muttered, rubbing at his eyes as though he could block out the memories of what his imagination had conjured up.

"We could do that" Jessica agreed "Though I was thinking of something with a bit more finesse involved. Don't worry about it Sam, when stage one is complete I'll let you know what stage two is. We've got this sorted." She smiled at it before she leaned back in the chair, pulling her textbook back over to her and picking her pen back up, the conversation clearly completed and over in her mind.

Sam watched her for a moment before he looked down at the table, tracing a pattern on the wood with his fingertip.

Somehow he was getting the feeling that this was going to end up being way more complicated then he had originally thought it would be. For a moment he wondered whether he should drop the entire thing and leave it to Dean but his mind brought up an image of Dean's face when he had seen Castiel.

His brother needed help whether he knew it or not and Sam was going to make sure that he got it.

* * *

Author Note

**Bless the pair of them, they mean well…**

**Thanks for reading **


	4. Don't make me threaten you

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned it the below work of fiction belong to me in any fashion. I am merely using them for my own entertainment purposes.**

Author Note

**Here's chapter four. **

**It was fun writing the dynamic between Chuck and Sam because I wanted to show the prickly friendship between them which was based mainly on snide comments, jokes and lots of teasing. It might not be the healthiest friendship out there but its still a friendship based on the fact that both of them get on with Dean and therefore put up with each other for his sake.**

**So yep lots of fun!**

**Enjoy**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam if determined he's going to get it.**

Chapter Summary

**Sam enlists some unwilling help…**

Overall Romances

**Castiel Novak/ Dean Winchester and Jessica Moore / Sam Winchester**

Chapter Romances

**Mentions of Castiel / Dean**

* * *

Chapter Four

Don't make me have to threaten you

* * *

Sam entered the coffee shop, his eyes automatically going to the counter to see whether he could see any sign of his brother. It was technically Dean's day off but his brother was known for coming in on those days to try and clear the backlog of small jobs which he had to do, normally making a note of the stock they had and what they needed or the books. Sam had no idea how Dean managed to balance so many figures in his head without the use of a calculator but he wasn't going to complain if it kept his brother occupied and out of his hair for a while.

The shop was surprisingly quiet for once with only a few customers seated at the table either talking to each other or working away on their laptop disregarding the world at large. Other then a few glances his way when he entered everyone seemed intent on ignoring him which was exactly what he wanted for this.

He walked across the room and leaned his body against the counter, resting his forearms against it as he watched Chuck work. The older man was fiddling about with on of the machine against the back wall so he had his back to Sam; a smile of amusement covered Sam's face briefly before he coughed loudly and spoke.

"Hello Chuck"

He grinned when the other man jumped, swearing to himself and barely managing to hold onto the mug which he held in his hand. He turned to face the counter, his blue eyes wide with shock before they narrowed as they focused on Sam's face. Sam couldn't resist raising his hand from the surface and giving the older man a quick wave.

"Jesus Christ Sam" Chucked breathed, glaring at Sam as though he wanted him to explode into flames. "What exactly are you trying to do? Give me a heart attack because you're going the right way about it that's for sure"

Sam lowered his hand again and merely shrugged, plastering a look of innocence on his face as he placed a hand on his chest directly over his heart.

"I'm hurt Chuck that you would accuse me of doing some thing like that to you" he remarked, ignoring the disbelieving snort which escaped Chuck at his words. He leaned across the counter, peering around the coffee machine to make sure that his brother was sitting crossed legged on the floor again doing an inventory. That little move had caught Sam off guard more then once in the past and he was determined that it wouldn't happen again, especially not with the topic Sam was going to bring up.

"Yeah I'm sure your heart is bleeding inside" Chuck remarked bluntly, putting his hand on Sam's shoulder and shoving him back. "Stop sprawling yourself over the counter which I've just spent ages cleaning Sam" he said, Sam rolled his eyes when Chuck continued to speak. "And if you're looking for Dean then you might as well save yourself the effort and stop. Your brother hasn't stepped foot in here today, at least not yet anyway." Chuck amended with a quick glance at the clock.

Sam raised an eyebrow fixing Chuck with a disbelieving look.

"You really expect me to believe that Dean hasn't been in yet?" he demanded "Are you sure that he just didn't come in before your shift and leave before you came?" Chuck shook his head.

"He might have done" Chuck said "But if he did then he must be invisible to escape the notice of both Adam and Charlie. The first thing they told me was that he hadn't been in, I think they were actually worried that he was ill or something" Chuck remarked before looking at Sam. "He isn't ill is he?"

"No he would have got in contact" Sam remarked in concern, ignoring Chuck for a moment as he fished out his phone and checked his messages, he had a few messages from some friends, one from Jessica and none from Dean. Frowning slightly he quickly typed a message to his brother asking if he was okay and pressed the send button. He pushed the mobile back into his jeans pocket before turning round to face the room, looking for anything else out of the ordinary when he saw nothing he turned his attention back to Chuck who was watching him as though he was a bomb which was about to explode into his face. "This works out great actually, I need to you about something and its better if Dean isn't here for it"

Chuck wary look became a full blown worried one, his hands gripping the side of the counter tightly.

"No" Chuck said flatly pushing himself away from the counter and Sam's reach. "Whatever it is that's about to come out of your mouth the answer to it is no, so save your breath and don't even bother asking" Sam watched as the older man crossed his arms across his face with a look torn between determination and sheer terror.

"Come on Chuck, there's no need to be so melodramatic" he stated. "For all you know I could be asking you to lend me a dollar to save the life of a needy child, how bad will you feel knowing you didn't help them?"

"I could survive it I'm sure" Chuck responded as he jabbed his finger in Sam's direction. "The last time I agreed to one of your mental plans Dean almost fired me. Do you know how hard it is to get a job at the moment? Of course you don't you're at Uni still, its almost impossible Sam and even if I did get one the boss isn't gonna be as good as Dean so the answer is no. Thanks for coming to visit but no."

"I think the key word there is almost. He almost fired you but he didn't" Sam said brightly a smile coming back to his face as he thought back to the party he had thrown in the coffee shop without Dean's permission. It had been going fantastic right up until the point that Dean had walked in, he had taken one look around, gritted his teeth and walked out back. Sam winced as he remembered the look in Dean's eyes when he had gone after him to try and explain, Dean had told him to go back outside and then proceeded to ignore Sam for a week. At first Sam had scoffed at the punishment but by the end of a week he had been begging Dean to talk to him again. The silent treatment from his brother was definitely something that Sam didn't want to experience again if he could possibly help it.

"Well that reassure me greatly" Chuck remarked with a shake of his head. "Look Sam if you're going to order something then order it otherwise let me get on with my work. Andy is on his lunch and its just me so I kinda need to crack on before the after lectures rush comes in"

"I'll have a large Vanilla latte with two extra shots of espresso on top" Sam said, looking at Chuck and unleashing his puppy dog look which had never yet failed to get him what he wanted. He was slightly miffed when Chuck merely ignored his look and began preparing his drink for him in a takeaway cup. "Ok enough of the games" Sam said with a sigh. "What if I told you that what I wanted to talk to you about was something for Dean, it's nothing to do with me at all."

Chuck paused in what he was doing and looked up, a suspicious look on his face as he searched Sam's eyes carefully.

"You want to ask me something which will help Dean out?" he repeated, Sam nodded.

"That's right, not me but Dean" Chuck remained silent, clearly mulling over the comment as he finished Sam's drink and passed it over to him, waving Sam's money away when he offered it.

"What exactly do you want to ask me?" he eventually said, picking up a clothe and wiping down the coffee machine, his eyes fixed on the task though Sam knew him well enough by now to know that he was listening to him.

"I want to ask you to watch someone for me, it's nothing sinister and it's not gonna get you fired either before you freak out" Sam said. Chuck looked up at him warily but didn't interrupt instead waiting to hear what else Sam had to say. "We both know that Dean doesn't really have a life outside of this place unless you count his other two jobs" he remarked watching as Chuck acknowledged his comment with a small knowing smile, for an instant Sam watched the older man in confusion before he shook it off "right?" he pressed.

"I wouldn't know" Chuck replied. "Your brother doesn't tend to gossip with anyone, especially not about himself or what he has been up to. Most of the time the most any of us can get out of him is that he's fine and that he had a good evening."

"Yeah that sounds about right" Sam agreed before he sighed, running a hand through his hair "Look as far as I can see Dean likes a guy who comes in here, you've probably served him. He's slightly smaller then Dean, pale, dark crazy hair and blue eyes? Got a really gruff voice like he needs some throat sweets or something ring a bell?" he demanded. Chuck shrugged.

"Maybe, we serve kinda a lot of people in here Sam" he pointed out. "Why do you care about him anyway?"

"Because I want to get him and my brother together."

"Why?" Chuck asked curiously causing Sam to roll his eyes at him.

"Why do you think Chuck? Because I want my brother to be happy" Chuck seemed to consider his words carefully before he spoke.

"Surely if your brother wants to be with the guy then he'll sort it out himself by asking him out. Why do you have to get involved, when that will just complicate matters and make it awkward? You don't even know if your brother or the other guy even like each other" he pointed out.

"Oh they like each other all right, that much is clear. If you think that it's something Dean will deal with himself then you clearly don't know him at all" Sam said pointedly "Dean is much too complex and complicated to ever do something simply. Hence why I'm here"

"Right" Chuck said, tilting his head to once side thoughtfully. "And how exactly am I meant to help you in your one man crusade to interfere in your brother's life?" he asked causing Sam to glare at him.

"All I want you to do is to look out for the guy, his name is Castiel. Watch him and tell me how often he comes in here, whether he comes alone with each other, does he pay attention to Dean, and does he try and talk to him. That's the kind of thing I want to know and for the love of God Chuck do it subtly, I don't want Dean to know what we're doing"

"Right so I'm to spy on the guy your brother likes for you so you can what? Talk to him? Tell him how great your brother is? Because surely he already knows how great Dean is if he's interested in him?" Sam shrugged.

"I haven't decided what I'll do with the information" he remarked.

"And say I was actually mad enough to go through with this plan for you what is in it for me?" Chuck asked simply.

"You'll be helping Dean out, remember him? The boss you actually like?" Chuck eyes narrowed as a slight flush came across his cheekbones.

"Anything else?" Sam leaned over the counter and smiled sweetly at him.

"If you do this then I won't make your life a living hell for the next few months. Think about it no comments, no pranks, I won't embarrass you nothing" he offered.

"And if I say no" Chuck asked. Sam's smile widened.

"Then it will become my sole mission to make your life a living hell for the next few months. There are always ideas floating around my head Chuck just begging to be used on someone." Chuck's eye twitched for a moment before he breathed out noisily and threw his hands into the air in defeat.

"Fine Sam, you win I'll be your watchdog for you but if Dean finds out I'll be telling him that it was all your idea" he said flatly. Sam shrugged.

"You do that Chuck" he said, lifting up his coffee cup and flashing Chuck a smile. "Thanks for my drink by the way, it's almost as good as Dean makes it" he turned and walked towards the door.

Stage one would soon be complete.

* * *

Author Note

**Four down, three to go… Onwards!**

**Thanks for reading!**


	5. Some Traditions are sacred

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**This has without a doubt been my favourite chapter of the whole story so far to write. I love writing the brother's relationship with each other, showing how much they care about each other without going over the top over it. Its been such fun!**

**I'm going to have to stop for tonight now but here's hoping that the next two are redone to be followed by a new chapter!**

**Enjoy!**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**It's Tuesday evening which means only one thing…**

Overall Romance

**Castiel Novak/ Dean Winchester, Sam Winchester/Jessica Moore**

Chapter Romance

**Sam Winchester / Jessica Moore**

* * *

Chapter Five

Some Traditions are sacred

* * *

Sam took the stairs two at a time, cursing the broken down lift which meant he was later then he should have been. He never meant to be late, especially not on Tuesday nights, but there was always something which would come up which stopped him from leaving his dorm room on time. An essay which he had to quickly proof read before submitting it the next day, a chapter in one of his textbooks which he had forgotten to read, his room mate suddenly needing to talk to someone about his crazy ass girlfriend and God knew what else. If Sam was a superstitious man then he would have sworn that something was always trying to stop him from being on time.

Dean always understood though when Sam arrived, hot and sweaty and panting out his apology merely shaking his head and stepping back allowing Sam to enter his sanctum and relax without a single one of the comments which Sam knew must have been bubbling beneath the surface desperate to get out.

It had been a tradition between the pair of them that Tuesday night was the one night they kept apart for each other, it didn't matter what else was going on they would always say no to it. Sometime they went out to the cinema, sometimes to the local burger bar so Dean could get a fix of his favourite cheese and bacon burger. Sometimes they ended up at Sam's dorm if he knew his room mate was gone for the evening playing video games but the majority of times they would end up here in Dean's two bedroom apartment which Sam lived in during the breaks.

Dean would cook them something to eat unless he was too tired in each case they would treat themselves to a takeaway to eat while they watch a marathon of movies, normally a horror or spy thriller. Dean had convinced Sam to watch all the Bond films from the beginning stating that they would blow his mind so they were currently half way through them. Sam had been looking forward to watching the next one though he didn't want to let Dean know that otherwise his brother would become unbearably smug. Sam would bring the beers with him and it would end up with him kipping over in his room there and having a great time.

It was without doubt Sam's favourite evening of the week, even better then the weekend in his eyes and it was often only the thought of it which got him through his hellish schedule for the day.

He pushed open the stairway door on the fourteenth floor and stepped into the corridor where Dean's apartment was situated on. He took a moment to catch his breath before he stuffed his hands in his coat pocket and walked down the hall way towards number seven.

He stopped outside it and banged his fist against the door, quickly pushing the sleeve of hi coat up so he could see the time. He was twenty minutes late, he pulled a face suddenly thankful that he had brought more beers then usual. The sight of a cold beer at the end of a hard day was normally enough to mellow Dean out. He frowned when the door remained closed and knocked again suddenly wondering whether he had his days wrong and it wasn't actually Tuesday.

The door opened revealing Dean, his brother looked as though he had actually managed to get some sleep, and he looked awake and had clearly just showered if his wet hair was anything to go by.

"Hey Sammy" he remarked with a wide grin. "About time you got your ass over here, get inside before all the hot air goes out, this apartment sometimes takes ages to heat up" Sam nodded, grinning back at his brother as he squeezed past him into the hallway. He dumped his jacket on the floor, kicking his trainers off before he made a quick detour into his room to dump his overnight bag. Glancing around him sighed, feeling the weight of the past few days lift off of him before he turned and headed towards the kitchen where he knew Dean would be.

"Something smells pretty damn good Dean" he remarked, sniffing the air in appreciation.

It always amused him no end that Dean was the cook of the family. No one ever believed him when he told them after they had met Dean. Apparently his brother was more the type of person you expected to find elbow deep in the engine of an old classic car covered in oil and grease then someone who would pour over baking and cooking books looking for the next big thing. Sam knew that Dean was considering offering hot cooked meals in the coffee shop but he was holding off for some reason.

Sam had asked him only once why he hadn't tried to make a career of being a professional cook when he clearly had enough skills for it. Dean had merely looked at him for a moment before he had laughed, shaking his head. He had pointed out that men like him didn't belong in a kitchen taking orders; they belonged in places where they were in charge. He had also pointed out that he would have probably have decked the head chef within minutes of being there and been fired anyway. Sam had considered his point and quickly agreed.

"Put the beers on the side Sam" Dean responded, opening the fridge door and pulling out to cool beers, swiftly taking the tops of them before holding one out to Sam who dumped his load onto the side and took the drink gratefully. "I'm just reheating some lasagne I made on Sunday" Dean commented jerking his head towards the oven before he took a sip of his drink, green eyes fixed on Sam with a look of growing concern. Sam waited until he lowered the bottle before speaking.

"What?" he demanded, taking a sip of his own drink while holding Dean's gaze. He raised a questioning eyebrow when Dean shrugged at him.

"Nothing" his brother replied. "I was just thinking that you look like complete shit, when was the last time you slept eight hours exactly?" he asked

"When was the last time you did?" Sam retorted. Dean rolled his eyes at him, placing his bottle on the side before he crossed his arms over his chest, and leaning back so his lower back rested against the smooth granite counter behind him.

"Sam" Dean said simply, tilting his head to the side though. It was enough though; the concern mixed with the familiar demanding expression was enough to have Sam's words spilling out of his mouth.

"I probably slept like five hours last night" Sam answered after a slight pause, reaching up and scratching his nose when Dean's eyes sharpened in a silent question which Sam answered with a sigh "slumped over my desk, resting on my textbook"

Dean breathed in deeply, his eyes moving away from Sam to stare at the side of him. Sam waited for the lecture he knew was coming but instead Dean merely looked curious.

"Normally you survive on less then that" he stated "You don't look like a walking Zombie then" A slight bitter laugh escaped Sam's mouth.

"Yeah but I normally don't have Professor Crowley twice in the same day either. The man is completely sadistic Dean, it's like he takes pleasure in trying to fuck us all up in anyway possible. The comments he comes out with towards us is that… I don't get how he gets away with it."

"Language Sammy" Dean remarked looking half concerned, half amused by Sam's outburst. He unfolded his arm and picked his bottle up again, one hand resting against the surface. "Why did you have him twice today then? You're not normally like this on a Tuesday so I'm guessing it's a one off thing or something? He asked. Sam nodded.

"It better be" he said fervently "The dude is a sick fuck that's for sure. He was covering Professor Turner's class; he called in ill or something. If you ask me he probably just had the hangover from hell. Get him the right drink and he can drink anyone under the table" he remarked.

Dean didn't bother hiding his grin as he pointed to the door leading from the kitchen.

"Go into the other room Sam" Dean instructed. "The lasagne is pretty much done now. I've put the next James Bond on the table so get it into the player and set up will ya? I've got to have an early one tonight so the sooner we watch it the better" Dean remarked pushing himself back into a standing position. "You want another beer?" he asked as he snagged a tea towel from the side. Sam glanced down at his half empty bottle with a considering look.

"Sounds good, I'll get them though, you get that out of the oven, I'm staving." He grinned at Dean, grabbing two more beers from the kitchen before he left his brother to it and headed towards the living room instead.

He breathed in when he walked into the room glancing around him with a small smile as he went over to the coffee table and picked up the DVD, opening it and walking over to the large TV set up Dean had. He really did love this apartment, it reminded him of Kansas somehow and the good times they had there. It was probably his favourite place to be. He inserted the disc, blinking in surprise when his mobile suddenly started vibrating in his jeans pocket.

Frowning he fished it out wondering who was calling him at this time, he only gave his number out to people he wanted to speak to and most of them knew not to bother him on a Tuesday night.

"Hello?"

"Hi Sam, its Jess. I haven't called at a bad time have I?" she asked, Sam grinned his hand automatically tightening around the phone at the sound of Jessica's warm voice.

"No its cool Jess, I've got a few minutes spare, you all good?" he asked, muting the TV. He threw the channel changer on the sofa before strolling over to the window and staring out at the surprisingly nice view that Dean had.

"Yeah I'm great thanks" she responded, Sam could almost picture her wide smile in his mind. "I'm just calling to see whether you spoke to the other workers at the coffee shop yet? You said you were going to see them yesterday but you never rang or texted to let me know if you had so I thought that I'd ring you to find out"

Sam smacked his hand to his forehead, pulling a face before he glanced back over his shoulder to make sure that Dean hadn't snuck into the room while his attention was occupied. He lowered his voice keeping his eyes on the door.

"I didn't speak to them all" he answered "But I did speak to Chuck and he's the best one for the job. He didn't want to get involved at first but I convinced him to give us a hand. He should have started watching today and he'll get the stuff we need for part two" he said turning back to the window briefly.

"That's great news Sam" she remarked. "Does he know what Castiel looks like though? Did he know who exactly you were talking about when you brought it up?" Sam shrugged his shoulders forgetting that she couldn't see the movement over the phone.

"It shouldn't be a problem Jess, I'm working a two hour shift tomorrow between two and four" Sam reassured her "Its always been between that time that I've seen the guy so hopefully he'll come in. I checked the rota and Chuck is working with me so I'll be able to point him out so he knows who he's looking for"

"Looks like you've got everything well in hand Sam" she remarked warmly. "Will Dean be at the coffee shop, it might be harder to manage it if he's there watching, your brother seems pretty observant to me"

"He is" Sam confessed "But its Wednesday afternoon and Wednesday afternoon is the day that Dean remains out back dealing with sums and figures. He's going to be completely occupied and completely out of the way!"

"That's good news" she replied absently, he could hear the sound of voices and laughter in the background and wondered briefly where she was. "Perhaps you will be able to speak to Castiel and get some information from him, nothing major of course but something, you know Dean like the back of your hand so you'll be able to tell straight away whether we can use the stuff you're learning from him. They'll thank us when it's all over and done with and they're happily together"

"I'm not so sure of that" Sam remarked with a laugh, he breathed in deeply and spoke, making sure his voice sounded casual and not desperate. "I don't suppose you fancy going with me to see a movie on Friday do you Jess?" he asked "There's quite a few on at the moment which look good and it might be fun, my treat?"

There was a moment's silence before she spoke quietly.

"I'm sorry Sam I can't make this Friday" she said apologetically "Me and the girls have already made plans and I can't back out of them now"

Same pulled a face, his shoulder slumping down in disappointment.

"Don't worry about it Jess" he forced himself to say. "It was only a suggestion, it's not biggie I-"

"I can do Thursday evening if you're around?" she interrupted "You buy the tickets and I'll buy the popcorn and the snacks, I'll even let you pick the movie" she offered.

"Yeah… yeah Thursday is good as well, I'm around from seven onwards" he said brightly, he would have to phone his friend who he was meant to be having a study session with but he was sure that Ash would understand.

"Great, I'll speak to you later Sam, text me and let me know how tomorrow goes or maybe I'll pop in. Bye"

"Bye Jess"

He closed his mobile, a wide grin coming to his face as he punched the air.

"Well looks like someone just scored himself a hot date for Thursday" Sam jumped turning round to look at Dean who was leaning against the door frame, holding two large steaming green bowls in his hands, his gaze fixed on Sam with a matching grin.

Sam stared back wondering with a shot of adrenaline how long Dean had been standing there. Had he literally just walked in or had he heard some of his conversation about him self. Sam stared at Dean but his brother's face was fixed in an interested look.

"Where do you plan on taking the lucky lady?" he asked, walking over to the table and placing the two bowls on it.

"Movies first and then maybe to a bar afterwards if she fancies it" Sam responded, rolling his eyes when he felt his face redden. Dean's grin widened at the sight though for once he didn't tease Sam over it, instead he merely shrugged.

"Well it's a classic date and she clearly likes you or she wouldn't have offered you an alternative to Friday. I think it's safe to say that you are in there Sammy" he remarked lightly heading back towards the doorway.

"Yeah?" Sam said "And when exactly have you had the opportunity to use it recently? He asked, Dean glanced back at him and winked.

"I never kiss and tell Sammy boy, I'm just getting some more parmesan, I know how obsessed you are with cheese" Dean answered before he walked out of the door, whistling to himself leaving Sam to stare after him with a half amused, half embarrassed look.

Shaking his head he walked back to the table, glancing down at the food and smiling. At least Dean was never stingy on his portion sizes.

He collapsed on the sofa, reaching across and grabbing the remote control un-muting the TV. Romance could wait until tomorrow. All he wanted to do now was to eat his home cooked lasagne with his brother while watching James Bond beat the crap out of people using witty one liner as he did.

After all Sam had his priorities right.

* * *

Author Note

**Much better!**

**Onwards I go **


	6. Why you sneaky little

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**This is the first time the story has changed from what it was originally. When I read through it again I found myself conflicted and I wondered whether writing so many stories in one day had affected the way I wanted this story to go. I felt like I had done Sam an injustice nearly turning him into the villain of the piece where a villain isn't needed or wanted.**

**I've never doubted once during the seven seasons of supernatural that Sam loves Dean, he has shown it in so many ways and so many times and yeah he's made some pretty horrific mistakes and there are things he's done which I can't forgive but he hasn't done it in the Matchmaker timeline and that's where I slipped up.**

**So here is the new chapter, how it should have been written in the first place.**

**Enjoy**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**Who wouldn't want a slice of Dean's home made cake…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**None really, just some wishful thinking.**

* * *

Chapter Six

You sneaky little...

* * *

"Ok seriously, why the hell is it this busy on a Wednesday afternoon? Aren't these people meant to be in lessons or at work or something? Am I asking for the impossible for wanting just one hour when we're not run off our feet and can actually breathe?" Sam demanded grumpily, reaching up and brushing his fringe away from his eyes, scowling when the piece of hair fell directly into the same position again.

He turned to look at Chuck, hazel eyes narrowing when he realised the older man was ignoring everything he was saying to him. His attention instead fixed on the long queue of customers which wasn't lessening no matter how quickly Sam made their drinks up. When Sam had agreed to do this shift for Dean he had been expecting a lazy couple of hours which he would spend talking to the customers and filling Chuck in on stage one of Operation Big Brother. He hadn't expected to be rushed off his feet, making drinks and simply trying to keep up and keep a smile plastered on his face.

He made an annoyed huffing sound before he turned his attention back to the coffee machine which was slowly becoming his nemesis.

Why he had ever thought for a moment that making coffee was a walk in the park was beyond him. If anything it was harder then studying law at times. The problem in his mind was the fact that every customer wanted something different and by different he meant complicated. They had to have extra espresso shots added in or taken away, the tea had to be a certain flavour and the tea bag left in for a certain amount of time, they wanted flavoured syrup added to the coffee and then there was Sam's personal pet hate. The crazy individuals who decided that they wanted an iced coffee with whip cream and sprinkles and god only knew what else when there was snow on the ground. Sam actually feared for their sanity as much as he feared for his own while he made the drinks up.

As far as he could see every table was crammed, all the chairs both squishy and wooden were taken to the point that there were people standing in small groups holding their coffee cups in hand. The air hummed with the sound of laughter and chatter almost drowning out the sound of the music which Dean played at all time to help create a soft, pleasant environment for people to chill out in. Sometimes Sam thought that Dean had managed it a bit too well.

What Sam really wanted to do was to throw the caramel latte he was making onto the side, kick the damn machine that was slowly making his life into a living hell and storm out of the back to the small office space where he knew Dean would be. He fantasised for a moment about grabbing Dean by the scruff of the neck and dragging him outside to take over while Sam downed a much needed vanilla latte to calm him down.

How the hell Dean managed to make the whole process look so easy and simple was a joke. His brother had the ability to produce the drinks almost as soon as the order left the customer's mouth and still managed to hold a conversation with them, charming them and producing a smile regardless of how pissed off the individual had looked when they first stepped into the coffee shop.

It was a skill which Sam quite frankly envied and wished he possessed at that one moment in time. He would take anything which would have made his life easier right then.

It was probably that level of service which was why the coffee shop was so popular with the local student and business population. Dean had played it perfectly, showing a level of business sense and skill which Sam hadn't known he possessed until he opened the coffee shop. It made sense to Sam when he actually thought about it. Who wouldn't want to have a perfect made beverage made for them by a good looking guy or a pretty girl? Who wouldn't want a slice of freshly baked cake which had been made that day and literally melted in your mouth? Who wouldn't want to collapse into one of the chairs which were so squishy and comfortable that they should have been illegal?

Dean was quite simply a genius in Sam's eyes though he would never go as far as to actually tell his brother that in case he was crushed by his brother's ego. Still there was a part of him that wished their father had lived long enough to see how wrong he had been about Dean all these years.

Sam bit down on his lip trying to ignore his bad mood. He wasn't pissed that he was working or that it was busy, if anything he was grateful for it because it kept him busy. What he was pissed at was the fact that it was so busy that it was keeping him from having a conversation with Chuck, a much needed conversation.

There was always the chance that Chuck remembered Castiel's name but Sam couldn't guarantee that the older man would be able to put a name to the face, especially if most shift he was on was as busy as this one. All the names and faces were simply becoming a blur to him.

"Hey Sam, are you actually gonna serve some drinks or are you just planning on standing there staring into the distance?"

Sam blinked at the familiar voice and turned to the side to see Chuck glaring at him, one hand resting on his hip, the other drumming a random impatient beat against the counter.

"What?" he said in confusion, Chuck made an annoyed face before he jabbed his finger at the line of cups waiting to be filled.

"That Sam" he stated "Wake up and get going"

"Oh those, yeah sorry about that" he muttered, grabbing the first cup and flipping the machine switch so a loud hissing sound filled the air.

"Do I need to go and get Dean to give you a hand since you're struggling so much?" Chuck asked with a raised eyebrow. There was a gleam in his blue eyes which made Sam believe that the older man was actually enjoying seeing Sam in this situation, flustered and off balanced. Sam met his gaze, pouring a butterscotch coffee into a middle sized takeaway cup.

"If you do that Chuck then I'm going to make you wish you had never been born" Sam answered, his voice light and cheerful as though he was sharing a joke with Chuck. He placed the lid of the drink on before glancing at the name scrawled on the side "Medium butterscotch coffee with an extra espresso shot for Ruby?" he called out, his eyes moving over the small crowd gathered at the end of the counter. A young, pretty brunette raised her arm, a smile coming to her face as her dark eyes moved over his face with a look of appreciation. He smiled back at her, passing her the drink before picking the next cup up.

"I was just checking" Chuck replied turning back to the counter with a smile for the customer who had just walked up.

Sam rolled his eyes and continued working, clearing the back log of drinks quickly, the last thing he wanted to do was let his brother down by tarnishing his well earned reputation for fast service. Once they were finally clear of drinks Sam straightened his body, moaning in appreciation when the bones in his back gave a satisfying crunching sound. He couldn't help but grin when he noticed from the corner of his eyes that the sound caused Chuck to flinch.

"Well that sounded healthy" Chuck grumbled. "You might want to get that checked out because that sound is not what a back is supposed to sound like." Chuck continued to say wiping down the surfaces, his eyes flickering between the entrance to the shop and Sam's face as though he was preparing himself for round two in a never ending war.

"It's called being a student Chuck, its kinda what happens when you're bent over textbooks and computers all day, Uni is a lot of things but being good for the back isn't one of them" Sam responded, he wiped down the machine before opening the top of it and glancing in, a curse escaping him when he realised that the machine was almost empty of coffee beans. There would be a riot if he didn't get it restocked. "I'm going to go and get more coffee beans Chuck, we're almost out. Are you going to be okay out here by yourself for a moment?" he asked.

Chuck bit down on his lower lip, scanning the shop carefully before he turned to Sam and nodded at him.

"Yeah I think I can cope, just don't take too long getting them ok? The next class comes out in like five minutes and this is their first pit stop they make" he advised. Sam nodded and headed out back towards the office where he knew Dean was holed up in and where some of the supplies which hadn't been put away yet were kept.

He stopped outside the closed door, knocking light on it before he pushed it open and stepped into the room with a quick glance around his eyes falling onto the bags which had been shoved in the corner.

"Hey Dean" he remarked casually "Just come to restock"

"Already?" Dean answered looking up from the books with a frown.

"What can I say" Sam replied with a shrug. "It's rammed out there."

He watched as Dean leaned back in his chair, twirling his pen in a strangely elegant manner between his fingers, a large smile coming to his face which made Sam stop in his tracks to shoot his brother a puzzled look. Now he looked closely at him Sam could see that Dean looked as though he was in a fantastic mood which was just strange. Doing the books normally put Dean into a foul mood, he would snap at anyone who disturbed him making it clear he wanted to be left alone.

"You know" Dean began, dropping the pen on the table surface as he sat forward and run his hand down his face. "I'm pretty much done here so if you wanted to shoot off early and get some stuff done then I can cover the last of your shift for you?"

Sam hesitated over the offer for a moment seriously tempted by it.

He knew that Jessica was in the library studying because she had mentioned it in the text conversation they had had in the morning. He had brought his bag with him in case he had fancied heading to the library once the shift was over, he could grab it and head over there now and hook up with her and maybe convince her to go to dinner with him afterwards. Or he could always go and finally get his hair cut. God knew it needed it, it had officially gone from fashionably scruffy to just plain scruffy. His growing beard and rumpled looking clothes which had seen better days wasn't helping his image anymore, if anything he was beginning to resemble a tramp.

However tempting the offer was he couldn't leave, not yet anyway since Castiel hadn't been in that afternoon yet. Sam needed to point him out to Chuck so he knew exactly who he was looking out for. Not only that but Sam had checked the rota that afternoon and he knew that Adam was due in to close the place up. If there was one person Sam wanted to bring into the plan then it was Adam Milligan. He had to be one of the most observant people Sam had ever met, if anyone would find something they could use it would be Adam. He knew the younger boy would do it as well because he knew that Adam looked up to Dean and admired him, he would definitely want to be a part of making Dean happy.

"Thanks for the offer Dean but I'm actually good thanks, I don't mind finishing the shift" he replied aware of the silence lingering between them. He shook himself mentally and walked over to the bag of beans, bending down and hoisting the heavy bag to his shoulder, moving it around until it was comfortable. "You should take the time to get some sleep because you're looking like death warmed up and that's not an attractive look for anyone."

Dean stared at him, watching as Sam made his way across the room and back to the door.

"Right" he said slowly "Who are you and what have you done with my brother? The Sam I knew normally can't wait to get out of here"

"Funny Dean" he remarked. "Believe it or not this is actually a welcome break from studying so I'm not letting you take it away from me. I'll come and say goodbye when my shift is over or something" he flashed Dean a smile and left the room heading back to the shop floor whistling a tune to himself suddenly in a much better mood.

He headed to the coffee machine, ignoring the grateful look Chuck shot him as he turned his attention to filling it up, once it was done he dumped the depleted bag on the back counter turning just in time to see the door open and for Castiel to walk in.

"Chuck" Sam hissed, his eyes widening before he reached out and smacked the older man's arm lightly and ignoring the yelping sound Chuck made in response. "That him, that is Castiel" Chuck rubbed at his arm shooting Sam a quick glare.

"I know it is Sam, I've always known who Castiel was" Chuck replied.

Sam stared at him, taking a step back as confusion filled him. Why the hell hadn't Chuck said at the beginning that he knew who Castiel was, it would have saved them all a lot of hassle.

He straightened just as Castiel reached the empty counter and looked at him carefully seeing him not as a customer but as a potential match for his brother. He was dressed in a suit with a white shirt, blue tie and a ratty looking tanned trench coat which had clearly seen better days. He looked like a tax accountant or a professor, definitely not Dean's normal type. Dean himself was the king of casual always dressed in jeans, t-shirts and shirts, the complete opposite of Castiel.

Sam tilted his head, his eyes narrowing slightly as the older man looked at the drink menu above their heads scanning it carefully with a considering look on his face. He looked back down, his eyes landing on Chuck before they moved to Sam and watched him carefully. Sam met the blue eyes directly trying to see what the attraction was but he gave up. He would never understand Dean's taste in anything least of all his love life. He looked away first, peering at him from the corner of his eye as Castiel focused on Chuck.

"I will have a- a vanilla latte please" Castiel remarked, hesitating briefly over his order.

"A vanilla latte?" Chuck repeated looking faintly confused by the order. "Don't you want your usual?" there was a friendly note to his voice which was normally lacking when Chuck dealt with other customers.

"Not today" Castiel answered. "Dean has told me that vanilla lattes are fairly nice and that I should broaden my horizons" a look which almost looked fond came across the older man's face but it was gone before Sam could be certain. "Is Dean in today?" he asked, his eyes flickering to Sam again.

"He's out back at the moment" Chuck replied, bending down and grabbing a medium sized mug from beneath the counter and passing it to Sam who took it, his mouth gaping open. "Do you want me to go out back and grab him? Sam can cover while I do" he offered. Castiel went to answer before he stopped and looked at Sam with a new level of intensity in the gaze which made Sam feel vaguely uncomfortable. He glanced down quickly and focused his attention on the mug in his hand.

"No, it's not important; I don't want to bother him if he's doing the books"

Sam eyebrows disappeared into his fringe, he glanced up sharply meeting the blue eyes watching him, making Sam wondered what exactly he was looking for.

Castiel had obviously been in here enough to build up a talking relationship with the staff here. He also knew that when Dean was out back he was doing books and he had clearly spoken enough to Dean for his brother to recommend other drinks, something Sam knew that Dean only did with the regulars who came in daily. The whole thing was intriguing and frustration in equal measure.

Sam wondered how much Castiel knew. Did he know that Sam was Dean's brother? Was that why he was staring at him because it was the first time he had properly seen him, knowing that he was Dean's brother. He knew Dean would have mentioned him, he always did. He would have to step the plan up a notch if they were already at this stage. He had to make sure that Castiel was good enough for Dean; he doubted his brother could deal with anymore rejection.

"One medium vanilla latte for Castiel" Sam remarked with a half smile holding the mug out to him. Castiel took it from him being careful not to touch him. He hesitated for a moment as though he wanted to say something to him but stopped himself instead thanking Sam. Sam watched as Castiel looked towards the door leading to the back with an almost wistful look before he turned and walked over to the table by the door, placing his drink on the empty table and sinking into the chair, closing his eyes for a moment before he pulled out some papers and his phone from his bag.

Sam looked away and looked towards Chuck with a raised eyebrow and a half curious, half threatening look on his face.

"You knew all along" he said flatly shaking his head. "Seriously dude you can be a dick sometimes" he stated "Now come on, spill the beans what do you know about him?" he asked. Chuck frowned.

"Not that much" Chuck answered; watching Sam warily as though he expected Sam to reached over and give him a wedgie.

"Well you probably know more then me" Sam pointed out.

"Well he rarely talks to anyone other then Dean" Chuck began thoughtfully. "He's polite to the rest of us but it's pretty clear that Dean is the one he wants to interact with. I don't know his surname but Adam did find out that he teaches Ancient History and classical studies at the university and that he's only just started this term."

"That's pretty good" Sam said frowning thoughtfully as he tried to figure out he could use the information. "Anything else?"

"He comes in twice a day, first thing in the morning and for an hour every afternoon between three and four. He gets a takeaway in the morning and sits in during the afternoon if he can get a seat. If he can't he tends to linger at the counter if Dean is working. He always orders a large Americano with an extra stop. This is the first time he has ever ordered anything other then that."

"Has he ever come in with anyone else?" Sam asked. Chuck shrugged.

"Once, he came in with a blond guy who sounded British" Sam nodded.

"Has he ever tried a slice of Dean's cake?" Sam suddenly asked with a wide grin. Chuck looked at him carefully before he shook his head.

"I've not seen him" he replied hesitantly.

Sam smirked.

"I think perhaps its time he did don't you think"

* * *

Author Note

**Next chapter will be completely different from what I thought it would be!**

**Hope you enjoyed this.**


	7. Just listen to me for once in your life

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**So completely different chapter for this one but I think it's alright.**

**It shorter then the other ones but it's almost a filler chapter, like an interlude, giving you another characters perspective on what is happening, this time round we're with Chuck which is interesting because I like the way I write Chuck.**

**It's one of the reasons I write in the first place because I love taking fairly two dimensional characters and turning them into something better and more realistic, so giving Chuck problems and a past is a good way of doing that.**

**I hope you enjoy it!**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**Chuck tried his best but some people can't be reasoned with…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**We're beginning to stumble towards Cas and Dean…**

* * *

Chapter Seven

Just listen to me for once in your life

* * *

"Wait Sam, just think about this for a moment, are you sure it's such a good idea?" Chuck asked, his eyes widening as he watched Sam walked over to the counter which displayed all their baked goods and stare down into it with a considering expression on his good looking face. Sam glanced back towards him, a look of determination in his eyes which caused Chuck to silently sigh. He knew that reasoning with Sam was going to be a battle which he was going to lose but he had to at least try and avert the disaster he could see looming ahead of them all..

"Why wouldn't it be a good idea?" Sam asked sounding curious while he tilted his head. He reached down into the display and lifted up a slice of lemon tart and a slice of the chocolate fudge cake which Dean had perfected down to a fine art. Chuck had tasted it once and nearly self combusted about how damn good it had tasted. It was no surprise to him what so ever that the fudge cake was their best selling cake. In fact the only thing he found himself vaguely surprised about was the fact that there was a slice of it left at all, normally it sold out the minute Dean brought it out, still warm and gooey and delicious. "Which one do you think he would eat?" Sam remarked looking at both cakes thoughtfully, clearly weighing up the pros and cons for each of them. He looked up, his eyes focused on Castiel before he replaced the chocolate cake on display. "Looks more like a lemon tart guy to me" he remarked quietly, clearly speaking to himself.

Chuck wanted to stop Sam from doing this, he wanted to tell the younger boy that approaching Castiel was a stupid idea but the one thing he had learnt about Sam Winchester was the fact that he had to be one of the most stubborn individuals Chuck had ever met in his life and that was saying something. Sam was the kind of guy that if you told him to do something and you couldn't give a good reason for it he would end up scowling at the person as though he wanted to rip their face off before digging his feet in refusing to budge. It wouldn't have surprised Chuck if Sam would have done it regardless just to spite him.

The only time Sam had ever backed down from a decision once he had made it was when Dean got involved. Sam listened to his older brother even if he rarely listened to anyone else. If Dean told him to do something or to drop an idea or subject then Sam would kick his feet, complain and throw a hissy fit or two but he would eventually obey.

Chuck didn't know much about the Winchester boys other then what most people knew. He knew for example that Dean was older then Sam by four years. He knew that they both lived in Kansas before they came here and settled down due to Sam gaining a scholarship at Stanford and he knew they were close enough that they could work together like a well oiled machine. Watching them both work a shift with each other at the coffee shop was something else. It was almost like they had the same mind they were so in tuned with each other.

But Chuck could see other things which perhaps others couldn't. There was something about them which pointed to them having a bad childhood, something which had brought them together so tightly. He knew that Dean had raised Sam himself. He didn't know how he knew only that little parts of their behaviour reflected it.

Chuck had spent the majority of his life watching and observing people seeing much more then what people expected him to see. It had always been the same way; he had learnt when he was younger to remain silent. If you were silent then people would tend to forget you were there with them even if you happened to be in the same room as them. He didn't mind if people ignored him, if anything he actually preferred it, making conversation and being forced to interact with strangers was a chore for him. Even working in the coffee shop was difficult but he made himself do it because he liked the people he worked with, he liked Dean and he even liked Sam when he wasn't fighting the urge to strangle the younger man.

It was easy for Chuck to view Sam as an annoying little brother; they seemed to share that sort of banter with each other. It was even easier to view Dean as an older brother even though he knew that Dean was six years younger then he was. It was the way Dean was from what he gathered, there was something about the other man which inspired confidence in the individual, as though he would be able to solve any problems which came up and would be willing to fight and defend the people he cared for. If Chuck needed to put up with the occasionally teasing remark or joke from Dean or Sam then he was happy to do so because it made him feel as though he belonged somewhere for the first time since his mother had died when he was ten.

It wasn't a feeling he was willing to give away, besides Dean trusted Chuck and Chuck wasn't going to let him down. He took a deep breath and tried again to talk Sam out of his decision.

"What exactly are you planning on doing Sam"? he asked turning to face him. The younger boy ignored him for a moment as he grabbed the whip cream from the small fridge where they kept the milk and sprayed it on the tart, his tongue peeking through his lips as he focused on his task.

"I would have thought that was pretty obvious Chuck" Sam answered placing the whip cream can on the counter and placing his hands on his hips, staring down at the tart with a considerate look as though he was trying to figure out if there was something missing from it.

"No I don't" Chuck snapped "You're seriously not going to just stroll on over there and give a stranger who you don't even know a free desert. What if he thinks you're coming onto him or something, what will you do then?" Chuck demanded desperately, flashes of imagery racing across his brain painting a vivid picture on how this whole scenario would end.

Sam hesitated for the first time, looking up from the plate to stare at Chuck instead, a hint of indecision in his eyes.

"He wouldn't believe I was coming onto him" Sam stated thought he sounded strangely tentative now as though he was beginning to see things from Chuck's point of view

"That's the point Sam, you don't know, he might view it that way" Chuck said, leaning against the counter. He glanced to the back door praying that Dean would suddenly come out, see what was about to occur and set his brother straight but instead the door remained stubbornly closed. Chuck turned his attention back to Sam. "I meant imagine if it was you in Castiel's place. There you are trying to enjoy your drink and get on with some work when suddenly some random sasquatch comes over and gives you a piece of cake on the house when you haven't even had a conversation with him before. I mean what are you going to think? I mean be honest Sam because I know what I would think"

"Ok so I would probably think the dude was coming onto me" Sam admitted unwillingly, looking away from Chuck and back down at the tart. He stared at it for a moment as though it held all the answers to the questions which were clearly racing around his head before he looked back at Chuck with a curious expression. "Why does it matter to you so much anyway?" Sam asked "why are you getting worked up over a piece of tart" his eyes suddenly sharpened. "You don't have a crush on Castiel do you?" he demanded, his voice going flat as his face turned suspicious.

"Jesus Sam, I know it's difficult but try not to be stupid. Of course I don't" Chuck responded instantly ignored the glare he received. "I'm just telling you because it seems strange. I mean if your brother likes him and he likes your brother then how bizarre is it going to be to receive a cake from the younger brother. I mean you don't even know what you're gonna say to him so it's just gonna be awkward for everyone involved, including me because I'll be forced to watch and it will be like a car accident, I won't be able to look away" he took a deep breath.

"Except the fact that I'm going to tell him that Dean told me to give him a slice of the tart if he came in. If they've spoken at all then he's gonna know who I am and it won't seem that strange that Dean has mentioned him to me."

"He hasn't though" Chuck pointed out.

"Yeah but Castiel doesn't need to know that does he" Sam responded. "Plus if they've spoken about drinks then they would have talked about the cakes. Dean might try and hide it but he's blatantly proud of everyone loving his baking."

"They might have Sam" he replied watching with a sinking feeling as Sam grinned widely at him.

"Well then it won't be weird if I tell him it was Dean's idea because he might not know me but he knows my brother. I'm merely the messenger, the fact I'm his younger brother will simply add to the non weirdness of it all because brothers talk right. It's gonna go great, you just need to stop worrying so much Chuck otherwise you'll end up with more grey hairs and wrinkles then you already have."

"I am not going grey" Chuck retorted resisting the urge to rush off to the staff toilets to check his hair in the mirror to make sure that Sam was wrong, sighing he threw his hands up into the air. "Fine if you're too stubborn to listen to advice when its given to you then that's your problem. I can't stop you doing this but don't come whining to me, wondering how it could have gone horribly wrong when it does because I'll simply tell you that I told you so and then leave you to Dean's tender mercies because he's gonna be pissed if he hears you've been harassing Castiel"

"Well it's a good thing then that Dean isn't going to find out" Sam responded offhandedly "Unless of course you're going to tell him?"

"I'm not telling him anything" Chuck replied in defeat. Sam shrugged.

"This isn't a big deal Chuck I don't get why you're freaking out. Its just a chance for me to find out more about the guy who potentially wants to date my big brother. It's my duty to make sure he's good enough for Dean" he grinned confidently at Chuck. "Wish me luck" he remarked picking up the dish and ducking out from behind the counter heading towards the table where Castiel was seated at.

Chuck watched him go with a sinking heart.

This wasn't going to be good, he just knew it.

* * *

Author Note

**Next chapter will be up tomorrow so look out for it**

**Thanks for reading **


	8. I'm not sure

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**So just in case you missed my Author note last night I have gone back over this story and pretty much rewritten it. I seriously and I do mean seriously recommend that you reread at least chapter six and seven if you haven't already done so because otherwise this chapter eight will make no sense in the context of things.**

**I felt like I was doing Sam the wrong way in this story so I decided to change it… so that's what I did. I think the story is at least eight thousand words longer then it used to be and I'm a great deal happier with this version so hopefully you will be as well!**

**Anyway below is the first interaction between Sam and Castiel… I'm sure that Sam had thought it would go so much better in his head… always the way**

**Anyway please enjoy!**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**Sam can't tell whether it went well or not…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**We're beginning to stumble towards Cas and Dean…**

* * *

Chapter Eight

I'm not sure

* * *

Sam walked across the room, swerving around the obstacles blocking his way while maintaining a smile on his face for the customers who tried to get his attention. His mind was completely focused on the task at hand as he mentally brushed off Chuck's concerns. What exactly did the older man think he was going to do here? Tell Castiel straight up that Dean fancied him and beg him to ask his brother out so that Dean would be happy and they could all move on?

Sam was a lot of things in this world, both good and bad, but being tactless over issues which required some level of sensitivity wasn't one of his flaws. He had inherited the charisma and charm which every male Winchester seemed to have had designed into their DNA code. The only difference between him and Dean was the fact that Sam was a great deal more particularly about whom he showed it to. Dean was happy to seduce the world at large, making men and women want to be with him. Sam hid it instead, preferring to save it for someone special, someone like Jessica for example.

He licked his lips and breathed in deeply, letting it out slowly as he tried to ignore the fact that he was beginning to feel extremely nervous. This was the guy his brother liked, his brother Dean who rarely showed a romantic interest in anyone because he was always too busy. It was suddenly extremely important to Sam that he made a good impression on the man in front of him. He actually cared for his brother, the last thing he wanted to do was ruin Dean's chances with Castiel because of some jackass move that Sam made.

Setting his shoulders, Sam reached the table, stopping next to it and speaking, making his voice friendly and relaxed.

"It's Castiel right?"

The older man looked up at him at the mention of his name, a flash of annoyance on his face which swiftly turned to surprise when he saw that it was Sam who had disturbed him. There was a moment's silence where they both seemed to measure the other person before Castiel spoke.

"Yes?"

Sam smiled pleasantly at him trying to ignore how awkward the whole situation felt. It had seemed like such a good idea when he had been behind the counter but now that he was actually doing it he wasn't so sure. God he would never hear the end of it if it turned out that Chuck had actually been right and that Sam should have actually listened to him.

Sam quickly glanced behind him at the counter to see Chuck resting both hands on the counter, leaning forward and staring at Sam's head, the minute their eyes met Chuck's expression turned supportive and he waved a hand towards Sam as though he was telling him to get on with it. Sam turned back and spoke.

"Yeah you don't know me and I know how awkward this is but my name is Sam Winchester. I'm erm Dean's brother, I'm hoping that if you've spoken to Dean like you said you have then you might know who I am otherwise this is just plain embarrassing and I'm gonna have to kill my own brother." He remarked, relaxing slightly when a small smile curved Castiel's mouth

"I know who you are Sam Winchester" Castiel answered, lowering the papers he still held in his hand to the table surface and fixing Sam with a thoughtful expression, his eyes moving over his face. "Your brother has mentioned you though I fail to see much family resemblance between the pair of you" Sam latched onto the conversation starter like a man who had been drowning.

"Dean is more like our mum, I kinda look like a mixture" he admitted before he continued to speak. "I guess you must speak to my brother quite a bit then. I haven't really seen you around here before" he probed lightly. Castiel shrugged his shoulder, a slight flush coming across his cheeks as he looked away from Sam for the first time, wrapping his hand around his mug and lifting it to his mouth. He took a sip, setting it back gently on the table before he spoke.

"Your brother is an interesting man to talk to Sam" he remarked casually. Sam nodded his agreement with the assessment.

"That he is, he's always been interesting. I think Dean knows a little something about everything though he tries to make out that he doesn't." Sam confided, surprised by how easy Castiel was to talk to. There was something about the older man which was calming and almost peaceful. As though you could tell him anything and he wouldn't judge you, he would merely listen to the end and then give you the advice you craved. It made Sam want to sit down opposite him, put his feet up on the table and confess everything to him. He wanted to tell him about his never ended work stream, about his desire to be with Jessica and his constant concern for his brother. Instead however he lifted the plate in his hand up.

"This if for you" he stated simply, leaning down and putting the plate on the table. He watched carefully as Castiel looked down at it, a small frown coming to his face before he met Sam's gaze with a puzzled look.

"I didn't order any cake" he said, Sam shrugged his shoulders.

"Oh I know you didn't" he replied offhandedly watching with a sinking feeling as Castiel's puzzled look melted into a frown. He hurried on before the other man could say anything. "It's just Dean mentioned last night how you hadn't tried on the cakes we sell here yet and he mentioned that if I saw you today then I should pick you a cake and give it to you on the house so you could give it a go and know what you've been missing out on."

Castiel's frown disappeared into a look of surprise and warmth as he turned back to look at the lemon tart.

"Dean asked you to bring this to me?" he asked his voice carefully neutral as he reached out and lightly grabbed the plate, dragging it across the table so it was in front of him.

"Yep" Sam said before he grinned widely "You know I don't know if he mentioned it but he actually makes all the cakes and stuff himself. He's always baking trying to keep up because they keep selling out. He's pretty good though I don't tell him that, no one tends to believe me when I tell them, I guess they look at him and decide it's not true"

Castiel looked up at him, picking up the fork Sam had provided him with. Sam could see a look of anger enter the blue eyes at his words which surprised him.

"It doesn't surprise me that Dean made these, he's a talented man" Castiel remarked stiffly, his gaze suddenly hard. "I'll be sure to thank your brother when I next speak to him for his generosity." Castiel tone made it clear that he was dismissing Sam, his gaze moving past him to the door where Dean was "Thank you for bringing me the tart Sam."

"Yeah no problem, I hope you like it Castiel" he remarked, turning and walking back over to the counter with a frown on his face. He actually had no idea how that had gone. Castiel hadn't revealed anything about himself to Sam, if anything it had been the other way round with Sam revealing things to the older man about his brother. Jessica had told him to get some information on Castiel but how was he actually meant to do that when the other man didn't speak about himself.

"Well how did the big epic plan go then?" Chuck demanded the minute Sam was back behind the counter with him. Sam glanced back to the table to see Castiel eating the tart with a look of surprised pleasure on his face.

"I don't actually know" Sam confessed, reaching up and running his hand through his hair as his nibbled at his lower lip thoughtfully. "I haven't done any harm if that's what you're thinking and I did find out that he knows who I am which points to him having more then one conversation with Dean because-"

"Your brother only starts bringing you into conversation from the third time onwards because by then he can tell if the person is worth keeping around." Chuck finished, Sam looked at him with a raised eyebrow, smiling slightly when Chuck went red.

"Oh" Sam remarked.

"What?" Chuck demanded looking embarrassed "Some of us actually pay attention to things which are happening around us" he said huffily, crossing his arms over his chest and turning the subject back to what they had been talking about before. "So did you learn anything else during your stealth mission which you can use in your operation?"

"He thinks Dean is an interesting man" Sam said, rolling his eyes when Chuck snorted.

"Most people do Sam" Chuck said bluntly, tilting his head as he considered Sam thoughtfully. "So what you're actually telling me if that not only did you go over there and find out nothing useful which you didn't know already but you also told Castiel that Dean told you to give him the cake on the house. So let me ask you this wonder boy. What are you going to do when Castiel thanks Dean for the slice of cake and Dean stares back and tell him that he has absolutely no idea what he's talking about. I'm not expert on the workings of Dean Winchester or Castiel's minds but surely the pair of them are going to put two and two together and realise you're scheming."

Sam stared back at him ignoring the sinking feeling in his stomach which Chuck's words produced.

"Err-"he began stopping when Chuck continued clearly on a roll.

"And not only that but what are you going to do when Dean demands an explanation from you because he both know he's gonna, are you going to stare at him like a fish out of water as well?"

"I'll think of something by then" Sam muttered looking away from Chuck and towards the door, thankful for the first time when it opened and admitted the next wave of customers who had clearly just finished in their classes.

He needed to talk to Jessica and he needed to talk to her quickly.

He just hoped that she would know what to do.

* * *

Author Note

**Next chapter will be up next weekend though I'm not sure what day!**

**Thanks for reading **


	9. You are so on!

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**Holy Moly I've just seen that this story has 122 people following it! That's crazy!**

**Thank you soooooooo much if you're one of the people who are, it means the world to me. **

**Just so you know there will be a companion piece to this story which will be done from Dean's perspective. I'll probably start writing it soon but just not yet so look out for it **

**Sorry for the delay in getting this chapter up, juggling stories and time isn't quite as easy as it used to be but I am trying, updates are probably going to be every two weeks now instead of weekly just so you're aware.**

**Anyway please enjoy!**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**Sam makes a bet with Jessica…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**Sam Winchester / Jessica Moore, mentions of Castiel Novak / Dean Winchester**

* * *

Chapter Nine

You are so on!

* * *

Jessica shivered in the cold breeze, stamping her feet against the matted snow as she stuffed her gloved hands into her pocket. She glanced around her, eyes lingering on the faces surrounding her as she wondered where the hell Sam was.

They had agreed to meet outside the local cinema at seven so they could catch a seven thirty showing, Jessica has no idea what film Sam had picked for them to view but she didn't particularly care either. She was quite happy to watch anything if it meant spending some alone time with Sam Winchester.

Jessica had liked him from the moment she had seen him across the room at a friend's dorm party in the first week of term. He had been laughing over something, a wide grin over his face his large hazel eyes sparkling in the dim light, his eyes had glanced over to her and she had been lost. He had been surprisingly shy at first though so she had had to work at him slowly, befriending people who were friends with him so she could join their group when they went out drinking or bowling. Slowly she had wormed herself into his life, spending more and more time alone with him in the library, eventually swapping mobile numbers with him and making sure she was available to talk or to see him if he rang or asked her to meet him.

The fact that this situation had arisen with his brother had been the God send she had been looking for to push their friendship up to the next level.

And now, after all her patience and hard work over the last three month he had finally asked her out on a date and he was late. She didn't know whether to be annoyed with him or merely amused.

"Hey Jess, Sorry I'm late" Jessica turned at the sound of her name, a smile coming to her face when she saw Sam jog up to him, a matching smile on his face as he came to a stop by her side. "I was talking to someone and I couldn't get away from them, seriously there are some people out there who can't take a hint!" he commented with a shake of his head.

"That's ok Sam, I literally just got here myself" she lied, "Shall we head inside? I don't know about you but I'm freezing." She commented, Sam nodded his head, a look of guilt coming to his face as he moved, holding the door open for her. "I would have got us the tickets to save time but I wasn't sure exactly which movie you had picked for us to see" she said, looking back over her shoulder at him.

"I'm not bothered by what we see" he answered glancing around them quickly as they walked away from the door and into the warm foyer. "I was thinking we could watch the new thriller which has just been released; I saw when I was checking times out earlier online that there was a showing starting at eight. We could buy the tickets now and then go for a quick drink before hand if you fancied it? Though you know if there was another movie you'd prefer to see then we can see that, I'm easy" he commented, tilting his head to the side with a questioning look on his face.

"The thriller and a drink sound pretty good to me" Jessica answered. "They have a bar here which is kinda nice, I've been here a few time with a few friends and it's always been good up there"

"Cool, well let's grab the tickets first" Sam said, taking his hands from his pockets and rubbing them together. "I've got these" he said when Jessica made a move to get her purse out of the small purse she had brought out with her. Sam placed his hand on her lower back, gently steering her to the small queue in front of the ticket office before he took his hand away, running his hand through his hair with a slight awkward expression on his face. Jessica felt almost sorry for him and decided to take pity on him.

"So you never said how yesterday went. Did you show Chuck what Castiel looked like?" she asked, surprised when Sam's cheeks suddenly flushed pink, an embarrassed look coming across his face as he shifted awkwardly on the spot, nervously stuffing his hands back into his pocket.

"Yeah turns out that Chuck already knew who Castiel was" he said. Jessica waited for more information but Sam remained stubbornly silent, a distant look on his face as though he was caught up in his own thoughts.

"Well that's a good thing isn't it?" she asked cautiously. "I mean if this Chuck guy already knows who Castiel is then it makes life easier, especially if they are on talking terms. He should be able to get some information out of him that we can use. I'm guessing that if the staff know him by name then he's gotta go there quite often, especially when you consider how busy your brother's coffee shop always seem to be" she pointed out. Sam breathed out and nodded his head.

"Yep according to Chuck, Castiel goes in there twice a day, once first thing in the morning and then he goes in there for an hour or so in the late afternoon. He's a professor of Ancient history and classical studies or something along those lines anyway. He's only started this term."

"Holy shit, he's Professor Novak" Jessica stated in surprise. "He's gotta be, it all fits in" Sam turned to look at her, a slight frown on his face,

"You know him?" he asked sounding confused, Jessica shook her head, opening her mouth to speak when Sam held up his hand. "Hold that thought a moment" he commented, sounding distracted as he stepped up to the counter and purchased their tickets from the bored looking cinema worker. He came back to her, placing his hand lightly around her elbow as he steered them both away from the growing queue, letting go of her and passing her over the ticket he had brought her. "We can get some snacks nearer the time if you fancy any" he offered. "Let's get to this bar then, I don't know about you but I could seriously do with an alcoholic drink of some kind."

Jessica nodded her agreement, frowning slightly as she led him up the spiral staircase which led to the bar situated above the cinema. It was fairly busy in there but they were able to buy their drinks and take one of the tables situated by the window giving them a view of the foyer below. Sam waited until she had taken off her coat and was settled before he spoke.

"So Castiel's surname is Novak then?" he asked. Jessica shrugged.

"Well I don't know for certain Sam" she said slowly. "I never made the connection before and I might be wrong but I've got this friend called Luis and he's taking that degree and he told me that they had a new teacher that term, covering someone's maternity leave."

"What does Luis think of him then? Do I know Luis?" he asked. Jessica hid a smile at the barely disguised jealousy in Sam's voice.

"Possibly, you might have seen him at a few of Brady's parties" she commented lightly. "We often hang out together. You should really come out with us one time, I'm sure the pair of you would hit it off straight away. Luis likes Professor Novak" she said, turning the subject back to the important one. "He says he's pretty quiet but he gives an interesting lecture, making the topic come alive which I'm guessing is pretty damn important when it comes to ancient history. Apparently quite a few of the girls in his class have a crush on him though he pays them no attention."

"Yeah, well that part is hardly a surprise is it" Sam said, running his hand through his hair before he reached down and picked up his beer, taking a sip from the glass before he met Jessica's eyes. "I'm thinking that the only person Professor Novak has eyes for at the moment is Dean."

"If Castiel and Professor Novak are the same person then I can speak to Luis and get some more information from him. I'll bring him into the coffee shop tomorrow afternoon. Did Chuck tell you when Castiel tended to come into the shop in the afternoon? Does he have a certain time or is whenever?"

"He said it was nearly always between three and four" Sam answered. Jessica nodded.

"I'm pretty sure Luis mentioned earlier that he was around all day tomorrow because he wanted to meet up in the afternoon. We could meet you in the shop say about two forty five, get ourselves settled at a table and wait for him to come in. Luis can always approach him for us, its not gonna seem weird if one of his own students approaches him while he's out." She stated, frowning slightly when she caught the sudden look of discomfort which came to his face as her words. "What is it?" she demanded.

"I erm… I actually approached Castiel yesterday" Sam said, dropping his gaze to his beer, rubbing his finger pad nervously against the side of the chilled glass. Jessica nodded slowly, ignoring the sudden sense if unease she felt at the way Sam was acting.

"And?" she prompted.

"Well I went up to him with a slice of cake and told him that Dean had mentioned that he had never had a slice of his cake before and that he wanted me to give him a slice if I saw him" he admitted uneasily.

"And did Dean tell you to give him the cake?" she asked, already knowing the answer before Sam had even opened his mouth to reply.

"Erm no" Sam said, pulling a face at his drink before he looked up at her. "It seemed like such a good idea at the time Jess, I thought I could give him the cake because it would give me a reason to start a conversation with him and to find some stuff out about him which he could use, but he got pissed off and kinda sent me on my way."

"Wait, he got pissed off with you and sent you away because you gave his a slice of cake for free?" she asked curiously. Sam shrugged.

"No, not really" he said slowly, a thoughtful look coming to his face. "He seemed pretty damn pleased with the cake especially when I told him that it had come from Dean. He got pissed off when I told him that people never believed that Dean made it. That was when he thanked me for bringing the cake to him. Man I should have actually listened to Chuck for once and just not gone over there. I mean he's gonna go and thank Dean the next time he sees him and Dean isn't gonna know what the hell he's talking about."

"Dean will cover for you I'm sure, he'll tell Castiel that he told you to do it even if its only to save you from looking like a deranged crazy person" she teased. "Beside, what you did shows Dean off in a good light and if Dean likes Castiel as much as you say he does then he's gonna use anything he can to help his case in convincing Castiel to go out with him. When Dean asks you what Castiel was talking about just tell him there was some sort of misunderstanding or something. I doubt Dean will push it, though that's just my opinion, you know him better then I do." She said. Sam nodded looking slightly reassured by her words.

"It was a complete waste of time though" he pointed out with a sigh, "I didn't learn anything at all about him, if anything I ended up telling him about Dean" he stated in disbelief. Jessica smiled, taking a sip of her wine as her eyes moved over Sam's face, he was nibbling on his lower lip and looked adorable.

"I wouldn't say it was a complete waste of time" she commented lightly, meeting his eyes when they moved to her with a questioning expression in them.

"What do you mean?" he asked. Jessica sighed, shaking her head.

"Sam, you've confirmed for us that Castiel definitely likes your brother, that's like one of the most important things which you could have found out from him, more important then finding out what he might like" she said.

"We already knew he liked Dean Jess or we wouldn't be doing this" Sam answered, raising an eyebrow when Jessica shook her head again.

"No we didn't Sam" she said bluntly. "We both assumed that he liked Dean because of the way we saw him acting towards him but we never actually had confirmation that he did. For all we know Castiel could have treated everyone the same way but due to what you found out we known that it isn't Dean is special to Castiel, he likes him.

"Ok rewind" Sam said, holding his hand out looking confused again. "How do you make out that? What makes you think that he's admitted to liking Dean because I was there and there was nothing about the conversation we had which indicated to me that he did!"

"You see Sam" Jessica said flashing him a bright smile. "This right here is the exact reason why I'm here because I pick up on things which you might not have. You said that Castiel sent you on your way after you told him that people had pretty much insulted Dean?"

"Insulted Dean?" Sam replied "Who?"

Jessica rolled her eyes.

"You said that no one believed you when you told them that Dean baked. You know what that says to me? It tells me that what you're really saying is that people look at your brother and the way he looks and don't believe he can do anything which requires some brain power and instead they believe he can only do macho things like fix a car. I mean baking is a hard skill to master, people don't think about it but I'm telling you that being able to bake as well as your brother can is a gift and yes before you ask me, I have eaten your brother's cake, repeatedly on several different occasions because damn they are good cakes."

"Ok I can see where you're coming from and how some people might view it that way but how exactly does that prove that Castiel likes him?" Sam queried.

Jessica briefly closed her eyes, hiding a sigh from the man opposite her. She really hoped he was worth all this effort.

"Think about it Sam, you told him that people didn't believe that Dean was the person who baked the cakes and Castiel took personal offence to it as though you had personally offended him. You don't get pissed off about what other people say about another individual unless you actually have something to do with the individual in question. Now as far as we both know Castiel and Dean only met for the first time earlier this week and Castiel at least, is already protective of your brother. He doesn't want to hear anyone insulting Dean to him, however unintentional it might have been. You were merely relaying information to him which you had been told and he took offence, sending you away even though you were only the messenger. You don't do that unless you care, to be honest though it was a bit of a stupid move on his part. If he's sensible and he does like your brother as much as I think he might do then he's seriously going to be kicking him self over doing it.

"Why?" Sam asked "Not being funny Jess but he wasn't the one who made a complete ass of themselves. Dean is gonna kick my ass when he finds out about it and he's gonna find out soon enough about it because Castiel plans to thank him in person for the cake."

"You'll think of something to tell Dean" she said dismissively before she leaned forward against the table, reaching up and hooking some loose hair behind her ear. "Castiel will be kicking him self because he sent you away." She replied to his first question. Sam breathed out suddenly looking frustrated.

"This whole conversation is making me feel thick" he stated. Jessica laughed at the pout on his face and shrugged.

"Don't worry about it, you are a just a man after all honey" she said with a wink. "Look Sam it's fairly simple when you think about it. Anyone with half a functioning brain knows that you are the most important person in your brother's life, the same way he's possibly the most important in your life at the moment?" she questioned, continuing to speak when Sam nodded at her. "Castiel has just sent the person most important in Dean's life away, in front of witnesses and if that small fact gets back to Dean then he's gonna be pissed because no one gets to treat you that way in his eyes."

"You know that seems a bit farfetched to me Jess" Sam said, wrinkling his nose up. Jessica shrugged again.

"Anything to do with romance and relationship is farfetched Sam" she said. "I mean we've all done crazy things in the name of them both. It wouldn't surprise me in the slightest if Castiel came up to you tomorrow and apologises if he spots you in the coffee shop, especially if Dean is there and watching. Never forget that Castiel wants to make a good impression on Dean and getting you on board with everything which is happening is the best way to do it. If you approve of him then that's half his battle won already because he knows that your opinion matters the most to Dean."

"You seem pretty confident over all of this, fancy making a small bet over it?" Sam asked, Jessica leaned back in her chair feeling intrigued at the sudden change in Sam's manner.

"Depends what the terms of the bet actually are" she answered, watching as Sam slowly smiled at her, resting his hand on the surface of the table.

"If you're right and Castiel does in fact apologise to me tomorrow then I will take you out anywhere you want to go. I'll do whatever you want to do on that day." He stated simply, lightly drumming his fingers against the table.

"Ok and what about if you happen to win and he doesn't apologise to you?" she asked with a smile of her own, her grip tightening on the stem of her wine glass.

"If that's the case then I take you out where I want to go and we do what I want to do with no complaining" Jessica met his eyes, raising an eyebrow.

"Sam Winchester is this your way of asking me out on a date?" she asked playfully. Sam shrugged.

"Do you accept the terms of the bet?" he asked, holding out his hand to her. Jessica glanced down at it before she reached out and grasped it in her own hand, ignoring the butterflies which exploded in her stomach at the simple touch.

"You are so on!"

* * *

Author Note

**Thanks for reading! **


	10. Whatever you're doing, stop it!

Matchmaker 101

By

Ava Brett

Disclaimer

**None of the characters mentioned in the below work of fiction belong to me in any shape or form. I am merely using them for my own entertainment purposes.**

Author Note

**Here's the next chapter for you.**

**I'm sorry for the slight delay in getting this chapter out to you but real life has stepped up a notch at the moment. There's a lot of stuff going on which is keeping me occupied and away from writing so I'm sorry if you've been waiting for this chapter. All I can promise you is the fact that I have no intention of abandoning this story so it most definitely will be finished just as I plan to do the companion story based on Dean and Castiel's views.**

**I've really enjoyed writing the banter between Luis and Jessica and writing Luis in general is so much fun, I've based him on a friend of mine who actually does act like this. Needless to say I've been embarrassed tons of time in the past!**

**Anyway please enjoy**

**x**

Overall Summary

**For years Sam Winchester has watched his brother work himself into the ground in a bid to support him. He's sacrificed everything and Sam is sick of it. When Dean meets Castiel in their coffee shop he's determined to get them together. Dean deserves something for himself and Sam is determined that he's going to get it.**

Chapter Summary

**He won't stop now, not when they are so close…**

Overall Romance

**Castiel Novak / Dean Winchester and Sam Winchester / Jessica Moore**

Chapter Romance

**Sam Winchester / Jessica Moore, mentions of Castiel Novak / Dean Winchester**

* * *

Chapter Ten

Whatever you're doing, stop it!

* * *

Sam sighed, glancing around at all the students moving around him, all of them intent on their own tasks. He shoved his hands into the pocket of his heavy winter coat, resisting the urge to check his watch for the fifteenth time in a few minutes, with a great deal of difficulty.

Where the hell was Jess?

Had she changed her mind about meeting him?

Sam had been positive that their date the night before had gone well. They had talked most of the night, almost missing their movie because they had been so involved in a debate over a comment one of their friend's had made about caffeine, it had been a ridiculous conversation to have and yet at the time it had seemed important or maybe it had simply been because she had been getting into it as well. Normally when he tried to start up these sorts of debates with other people they would merely look at him as though he was losing his mind before they would make an excuse and scamper away. Even Dean would sometimes watch him with a raised eyebrow when he went off on one, calling him weird before he went and got them another beer to drink.

When they had eventually parted ways it had been nearly one in the morning and Sam had almost invited her back to his before he had bit down on his tongue hard. The last thing he wanted to do was cheapen the evening no matter how much he might have wanted it. Dean had taught him better then that, if he wanted to win Jessica over and convince her that he was the guy for her then he would have to take it slowly with her instead of rushing head long into things. It was frustrating but he knew that it would be worth it in the end.

"Sam!"

Sam glanced up at the sound of his name, a grin coming to his face when he saw Jessica weaving in and out of the crowd heading straight towards him, a matching smile on her face when her eyes met his. She raised her arm above her head and waved at him.

Sam's eyes moved over her face, his smile softening at the sight she made, she looked absolutely freezing, bundled up tightly against the cold, her exposed cheeks and nose red from the sharp, biting wind blowing around them. She looked adorable.

Sam bit back a groan as he shook his head. He must have it bad if he was already thinking like that. Dean would have a field day if he found out.

"Hey Jess" he called back, taking his hand out of his pocket and returning her wave as he took a few steps forward and met her, his smile widening into a grin when she threw her arms around him and hugged him tightly before she stepped back, tilting her head back so she could peer into his face.

"Sorry about that" she stated, looking down from him and glancing around her with a searching look. "You just look so freaking warm that I couldn't resist. I'm sorry I'm late as well; I was just speaking to my Professor after class and time kinda escaped from me. You weren't waiting a long time for me were you?" she asked.

"Five minutes or so" Sam lied with a shrug. "You ready to head over to the coffee shop? I don't know about you but I could just about kill for a Vanilla latte right about now, especially as I know for a fact that Dean is behind that counter today meaning its gonna taste like heaven!" he remarked, raising an eyebrow when Jessica shook her head at his suggestion.

"You can keep your Vanilla latte" she stated. "All I want right about now is a Hazelnut hot chocolate with loads of whip cream squirted on the top of it. In fact the thought of seeing you and having that hot chocolate has been the only thing which has kept me going throughout today, its been a complete and utter nightmare" she said with a sigh, reaching up and tucking some hair behind her ear before she wrapped her arms around her self and squeezed. "Beside we can't go yet Sam, we're still waiting for my friend Luis to appear. He's meeting us today remember?" she asked, glancing up at him with a questioning look. "We spoke about it yesterday before the movie?"

"Yeah I remember the one now" Sam replied resisting the urge to pull Jessica into a hug again. "Luis is the guy you said had a class with Castiel right?"

"That's right" she replied "But I did say that I thought they did. We're not even sure whether Castiel and Professor Novak is the same individual yet. For all we know Sam they could simply be two separate random guys who just happen to work in the same department and share a similar history as each other" she remarked, a twinkle coming to her eyes." Anyway Sam I just wanted to let you know that I had an awesome time last night" she said, her eyes sliding away from his as she nervously licked her lips. "I don't suppose you fancy doing it again some time soon would you?" she asked.

Sam remained silent, waiting until she shot him a quick look before he smiled widely at her.

"What exactly do you have in mind?" he asked. Jessica's shoulders suddenly relaxed as she stood a little taller, a look of relief passing over her features before she shrugged her shoulders at him.

"Well there is this new Italian place which opened up about a month a go or so in the main part of town, I can't remember for the life of me what its called but I do remember that its kinda near your brother's coffee shop maybe a few streets over or something. Anyway I was thinking if you were up for it that we could go out there for dinner one night? Do you even like Italian food?" She asked him curiously.

"Love it" Sam confirmed "Dean went through a stage where all he would cook for us was Italian food, we literally had a new Italian dish every day until he was satisfied that he had perfected them all. If I wanted something more then beans on toast then I had to be his guinea pig" Sam remarked, grinning when Jessica laughed.

"Well the place has been rated highly so I thought we could meet up outside the coffee shop maybe tomorrow at six and head over there and eat" Sam nodded.

"Tomorrow is cool with me" he said "Though it's my treat" he raised an eyebrow when Jessica opened her mouth to argue with him. "Don't even bother Jess, I can be a stubborn git when I want to be and this is one of those times, just ask Dean if you don't believe me, I'm sure he'll love to tell you all about it. God knows he has hundreds of stories about how I ran him ragged when we were younger." He remarked with a laugh as he shook his head. "God knows how the hell he managed it because I doubt I could have" Sam commented, glancing to the side of him with a thoughtful look. He was aware of Jessica watching him for a moment before she spoke, a rare gentle tone to her voice which he hadn't heard before from her.

"Your brother raised you, didn't he Sam" she stated, her tone making it clear that her words weren't a question but rather a statement she was making. "That's why it's so important to you that he's happy. You want to repay him for what he did for you when you were younger." Sam blinked, looking back at her with wide eyes. There was an awkward silence between them, Sam breathed out shakily, cursing him self for speaking so freely in front of Jessica. Their childhood was something that neither he nor Dean spoke of even to each other. They certainly didn't speak about it to others. Sam opened his mouth to say something when another voice spoke.

"Well, well, well Jessica Moore! Aren't you a sight for sore eyes" Sam watched, his mouth falling open slightly when a boy, slightly older then he was, came up to them, throwing his arms around Jessica and lifting her into the air, twirling her round. Sam's eyes narrowed at the sound of her laughter.

"Put me down you idiot before I throw up all over you!" she said, swatting the boy on the arm when he swiftly placed her back on the pavement. She turned to Sam who was watching them and gave him an apologetic look. "Sam this is my friend Luis Sanchez, Luis this is Sam Winchester" she introduced. Luis turned to him, his dark eyes assessing as they moved over him before he suddenly grinned, banishing the serious look from his face as though it had never existed. Sam watched as Luis took a step towards him, his arm outstretched.

"So you're the famous Sam Winchester then" he stated, shaking Sam's hand firmly when Sam's hand curled around his before he released it. "It's great to actually met you in the flesh, our dear Jessica talks about you a lot, to be frank its getting kinda boring, no offence intended towards you of course" Luis remarked breezily. "It's just a relief to know you actually exist and you're not someone who Jess created in an attempt to stop us matchmaking her with men."

Sam glanced towards Jessica, a grin coming to his face when he noticed that she had gone bright red at Luis's words, looking torn between killing Luis with her bare hands or running a mile away from the both of them.

"Well if you've finally finished embarrassing me Luis perhaps we could go to the coffee shop now and see whether the mysterious Castiel and Professor Novak are the same person or not." Luis grinned at her, reaching over and ruffling Jessica's hair with his hand before he threw his arm over her shoulder and began steering her in the direction of the coffee shop.

Sam stared after them for a moment, Jessica hadn't been kidding when she said that Luis was one of a kind.

"Come on Sam" Luis called over his shoulder with an impatient look. "While we're still young would be good." Sam blinked; shaking his head as he hurried after the other two, coming up on Jessica's other side. "So tell me Sam" Luis commented, taking his arm away from Jessica's shoulders and burying his hands into the pocket of his leather jacket, his shoulders hunching up slightly against the wind. "What's your major?"

"I'm studying law" Sam answered back "What?" he demanded suspiciously when Luis suddenly shot him an amused look over the top of Jessica's head.

"You studying law translate into you being a stubborn git who doesn't know when to back down" he remarked lightly with a wink in Sam's direction. Sam stared at him for a moment before he shrugged his shoulders.

"I wouldn't say I was all that stubborn-"he began to say, stopping when Jessica let out an unladylike snort from next to him. She glanced up at him with a mischievous look on her face.

"Oh I'm sorry Sam, I didn't realised you were actually being serious, I thought you were joking" she commented, turning to look at Luis "Sam here is extremely stubborn" she confided "And perhaps the slightest bit deluded if he thinks he isn't" she slipped her arm through his, squeezing his lower arm with her hand to soften her jokey words.

Luis glanced between them, a flicker of understanding coming to his eyes before he shrugged.

"Well that right there might be the pot calling the kettle black" Luis replied "I doubt there's a human being on the face of this planet who is as stubborn as you are once you get going on something Jess" he met Sam's eyes. "Don't let the sweet looking face fool you Sam. She's like a mule, kicks like one as well if you get her pissed off enough" he advised, stepping back quickly to avoid Jessica' foot. "See what I mean, a completely unprovoked attack! Pray tell me what I did to deserve that?"

"Please you know exactly what you did to deserve that" Jessica responded, shaking her head at him. "You're lucky that we need you today or I'd send you home for misbehaving" she commented. Luis held a hand to his chest with an injured look as he shook his head back at her.

"This is what I get for answering your call for help? A ton of abuse?" he stated. "You should be thanking your lucky stars that I'm such a kind and giving person to even accompany you to the coffee shop. Speaking of which by the way we're actually here." Luis commented, stepping in front of them both and opening to the door, moving to the side and making a gesture for them to go into the coffee house first. "After you monsieur and mademoiselle" he remarked innocently.

Sam shot him a suspicious look before he entered the coffee house, his eyes automatically closing as the familiar smell hit them. He opened them slowly, taking a few steps forward so Luis could step in behind them and close the door, blocking out the cold air. Sam rolled his shoulders, felling the tension ease from them as he looked around the crowded shop, his eyes meeting Castiel's almost instantly.

The older man was watching him from the same seat he had been in the last time Sam had seen him with a thoughtful look on his face. Sam watched as Castiel leaned back in his seat, his eyes flickering from Sam to Jessica before they lowered to their linked arms. Sam could have sworn that a look of amusement past over Castiel's features but the expression was gone before he could tell for sure.

Instead Castiel merely nodded his head in Sam's direction in a silent greeting before he looked away from him towards the counter instead. Sam automatically followed the line of his stare, stopping when he met a pair of watchful green eyes. Sam swallowed making him self meet the stare head on. Something was troubling his brother, he could just tell.

"I don't mean to break up your staring competition with the dude behind the counter but your Castiel is definitely Professor Novak" Luis said quietly from just behind him. Sam glanced away from his brother to meet Luis dark eyes over his shoulder.

"You sure about that?" he asked, Luis nodded his head.

"Positive" the other boy replied. "Let me grab myself a drink and then I'll head over there for a word. Jessica said last night over the phone that you wanted to gather some information about him or something similar?" he queried.

Sam nodded his head, glancing back towards Castiel, his eyebrow quirking when he realised that the older man was still staring at his brother. He glanced sharply towards Dean, surprised to see his brother leaning on the counter, his gaze fixed on Castiel. If Sam hadn't of known better then he would have sworn that the pair of them was having a conversation in their minds.

"Lets go and get a drink Sam, I don't know about you but I'm pretty thirsty" Jessica prompted, using her grip on his arm to drag him away from the door and towards the counter. Sam allowed him self to be moved, stopping in front of Dean who turned away from Castiel to look at him. Dean remained silent for a moment, searching Sam's eyes before he turned to Jessica and spoke, a small smile coming to his face.

"Hiya, what can I get you today?"

"We will have a large hazelnut hot chocolate with tons and tons of whip cream on it, a large caramel latte and a large vanilla latte please" Dean nodded.

"Anything else?" he asked.

"You've twisted my arm, I'll have a slice of your lemon tart as well, it's just too damn good to resist" she commented. Dean smirked at her.

"Glad to hear it" he responded "Adam" he called out, turning away from them and looking at the young blond man who was serving drinks to another customer. "Would you mind getting this order for me? I've just gotta speak to Sam in private for a moment."

"Sure thing Dean" Adam replied, flashing them all a smile before he grabbed two large mugs from beneath the counter and started up the coffee machine.

"I've just gotta borrow your boyfriend a moment Jessica" Dean remarked, looking back at them. He met Sam's eyes and jerked his head towards the end of the counter, a look in his eyes which stated that he expected Sam to obey him for once. Sam swallowed, watching Dean walk away before he slowly disentangled his arm from Jessica's, shooting her a reassuring look before he headed over to the end of the counter where Dean was waiting for him with an impatient look.

"What's up?" Sam asked.

"You know the funny thing about raising you Sam if that I know all your little tricks, mainly because I was the idiot who taught them to you in the first place. I always know when you're up to something and I know you're up to something now and I want you to stop whatever it is you're doing" Dean stated, a rare stern note to his voice which was reflected in his brother's eyes.

"I don't know what you're talking about, I'm not up to anything" Sam responded with a shrug.

"Don't play dumb Sam, it doesn't suit you. Cas told me about the cake thing today and how you gave him a piece and told him that I told you to give it to him. If that's not up to something then what the hell is?" Dean demanded. Sam raised an eyebrow.

"It's Cas now is it?" he asked, watching in surprise when Dean suddenly blushed, the red making his freckles stand out.

"Just shut it" the older man stated, looking uncomfortable. "I'll be watching you closely now Sam. I just thought I'd give you a chance to stop now before I'm forced to do something, like embarrass you in front of your new girlfriend, because if anyone can then its me"

"Jess isn't my girlfriend Dean" Sam replied, pulling a face when Dean gave him a disbelieving look.

"Yeah you keep telling yourself that Sam" he remarked, shaking his head before he turned and walked away, leaving Sam staring after him. He glanced back at Castiel, unsurprised to see the older man watching Dean's progress back towards the coffee machine with a look that made Sam shake his head.

There was no way he was going to stop now.

Not when they were so close.

* * *

Author Note

**Thanks for reading!**


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